Category: 100058-61-5

With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.100058-61-5, name is 3-(Benzyloxy)cyclobutanol, molecular formula is C11H14O2, molecular weight is 178.23, as common compound, the synthetic route is as follows.Safety of 3-(Benzyloxy)cyclobutanol

Example lbb – Preparation of R Synthesis of 2-bromo-l-(bromomethyl)-l-(phenylmethoxy)ethane [0299] The mixture of 1 (60.1 g, 0.47 mol), benzyl bromide (80 g, 0.47 mol) and Hg2Cl2 (100 mg, 0.2 mmol) was heated to 150 C over night. TLC showed the reaction was completed. The product 2 (98 g, 70% yield) was obtained by distillation (180 C) in vacuum as a colorless oil. [0300] 1H NMR (400 MHz, CDCl3):7.37-7.28 (m, 5H), 4.65 (s, 2H), 3.82-3.77 (m, 1H), 3.56 (d, 4H, J=5.2 Hz). Synthesis of l-(methylsulfinyl)-l-methylthio-3-(phenylmethoxy)cyclobutane [0301] To the mixture of 3 (45.1 g, 0.36 mol) in THF (400 mL) was added n- BuLi (145 mL, 0.36 mol, 2.5 M) at -10 C under N2 drop wise. It was stirred further 2 h at this temperature. And then it was cooled to -78 C and the mixture of 2 (46.2 g, 0.15 mol) in THF (100 mL) was added drop wise over 0.5 h. The result mixture was stirred further 2 h at – 78 C and over night at r.t. It was quenched by the addition of H20 (100 mL) and the mixture was extracted with EtOAc (300 mL*3). The combined extracts were dried over Na2SC>4 and concentrated in vacuo to give the crude product. It was purified by column chromatography (Eluan: EtO Ac/Pet. ether= 1/2, v/v) to give the product 4 (30 g, 73% yield) as a yellow oil. [0302] 1H NMR (400 MHz, CDCl3):7.36-7.26 (m, 5H), 4.47 (d, 2H), 4.38-4.31 (m, 0.6H), 4.21-4.18 (m, 0.4H), 3.10-2.98 (m, 0.8H), 2.78-2.64 (m, 1.2 H), 2.55 (s, 1.2 H), 2.44 (s, 1.8 H), 2.42-2.15 (m, 2H), 2.12 (d, 3H). Synthesis of 3-(phenylmethoxy)cyclobutan-l-one [0303] To a solution of compound 4 (30 g, 0.1 1 mol) in dry ether (500 mL) was HC104 (22.5 mL, 35%) at 0 C drop wise, while keep the temperature bellow 10 C . It was stirred further 2 h at 0 C and over night at r.t. Solid NaHC03 and MgSC>4 were added and the resulting mixture was stirred further 0.5 h at r.t. It was filtered and the cake was washed with ether. The filtrate was concentrate in vacuo to give the crude product. It was purified by column chromatography (Eluant: EtOAc/Pet.ether=l/4, v/v) to give the product 5 (14.0 g, 72% yield) as a yellow oil. [0304] 1H NMR (400 MHz, CDC13): 7.39-7.25 (m, 5H), 4.52 (s, 2H), 4.40-4.34 (m, 1H), 3.26-3.10 (m, 4H). Synthesis of 3-(phenylmethoxy)cyclobutan-l-ol [0305] To the mixture of 5 (14.0 g, 79.46 mmol) in EtOH (150 mL) was added aBH4 (3.32 g, 87.40 mmol) at 0 C over 0.5 h. The resulting mixture was stirred further 2 h at 0 C and TLC showed the reaction was completed. The solvent was removed in vacuo and the residue was diluted with MeOH (100 mL) and quenched by HC1 (1M). The organic solvent was removed in vacuo and the residue was extracted with EtOAc (200 mL*3). The combined extracts were dried over Na2SC>4 and concentrated in vacuo to give the crude product. It was purified by column chromatography (Eluant: EtOAc/Pet.ether=l/4, v/v) to give the product 6 (14 g, 99% yield) as a yellow oil. [0306] 1H NMR (400 MHz, CDC13): 7.39-7.27 (m, 5H), 4.43 (s, 2H) 1H), 3.68-3.59 (m, 1H), 2.76-2.67 (m, 2H), 2.37 (br, 1H), 2.05-1.89 (m, 2H). Synthesis of 5-(phenylmethoxy)-2-[3-(phenylmethoxy)cyclobutoxy]pyrimidine [0307] To the mixture of 6 (10.5 g, 58.93 mmol) in DMSO (100 mL) was added NaH (3.06 g, 60%, 76.61 mmol) at r.t. The resulting mixture was stirred for 0.5 h at r.t, and then the mixture of 7 (13.0 g, 58.93 mmol) in DMSO (50 mL) was added drop wise over 10 min. The whole mixture was stirred further 0.5 h, TLC showed the reaction was completed. It was quenched by the addition of H20 (200 mL) and the mixture was extracted with EtOAc (200 mL*3). The combined extracts were dried over a2S04 and concentrated in vacuo to give the crude product. It was purified by column chromatography (Eluant: EtOAc/Pet.ether=l/5, v/v) to give the product 8 (10.0 g, 47% yield) as a white solid. [0308] 1H NMR (400 MHz, CDC13): 8.19 (s, 2H), 7.38-7.25 (m, 10H), 5.05 (s, 2H), 4.76-4.68 (m, 1H), 4.43 (s, 2H), 3.82-3.75 (m, 1H), 2.87-2.81 (m, 2H), 2.24-2.17 (m, Synthesis of 2-(3-hydroxycyclobutoxy)pyrimidin-5-ol [0309] To the mixture of 8 (8.84 g, 24.42 mmol) in dry DCM (250 mL) was added BC13 (100 mL, 1M in DCM, 0.1 mol) at -20 C under N2. The resulting mixture was stirred further 0.5 h at -20 C . TLC showed the reaction was completed, and then it was quenched by the addition of MeOH (20 mL). The solvent was removed in vacuo to give the crude product. It was diluted with DCM (50 ml) and the solid was filtered out by filtration. The cake was suspended in H20 (20 mL) and filtered, dried in vacuo to give the product (2.2 g, 50% yield) as a white solid. [0310] 1H NMR (400 MHz, DMSO-d6): 9.76 (s, 1H), 8.12 (s, 2H), 5.07 (br, 1H), 4.59-4.52 (m, 1H), 3.85-3.78 (m, 1H), 2.76-2.72 (m, 2H), 1.91-1.85 (m, 2H). LCMS [mobile phase: from 50% water (0.1% TFA) and 50% CH3CN to 5% water (0.1% TFA) and 95% CH3CN in 6.0 min, finally under these conditions for 0.5 min.] purity is >95%, Rt = 1.84 min; MS Calcd.: 182.2; MS Found: 183.1

At the same time, in my other blogs, there are other synthetic methods of this type of compound,100058-61-5, 3-(Benzyloxy)cyclobutanol, and friends who are interested can also refer to it.

Reference:
Patent; TRIUS THERAPEUTICS INC.; LAWRENCE LIVERMORE NATIONAL SECURITY, LLC; BENSEN, Daniel; BORCHARDT, Allen; CHEN, Zhiyong; FINN, John, M.; LAM, Thanh, To; LEE, Suk, Joong; LI, Xiaoming; TARI, Leslie, William; TENG, Min; TRZOSS, Michael; ZHANG, Junhu; JUNG, Michael, E.; LIGHTSTONE, Felice, C.; WONG, Sergio, E.; NGUYEN, Toan, B.; WO2014/43272; (2014); A1;,
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The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 100058-61-5, name is 3-(Benzyloxy)cyclobutanol. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of 3-(Benzyloxy)cyclobutanol

DEAD (1.35 mL, 5.73 mmol) was added dropwsie to a solution of crude product (1s,3s)-3-(benzyloxy)cyclobutan-1-ol (1.02 g, 5.73 mmol), 3,4-difluorophenol (821 g, 6.3 mmol) and triphenylphosphine (2.26 g, 8.6 mmol) in dry tetrahydrofuran (20 mL) at 0 C. The reaction mixture was placed under nitrogen atmosphere and stirred at 80 C for 15 h. The solvent was removed under reduced pressure, and the resulting residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate = 80:1 as eluent) to get 4-(anti-3-(benzyloxy)cyclobutoxy)-1,2-difluorobenzene (1.116 g, 68% two step yield) as faint yellow oil. 1H NMR (300 MHz, CDCl3) delta 7.39-7.25 (m, 5H), 7.08-6.99 (m, 1H), 6.63-6.56 (m, 1H), 6.51-6.44 (m, 1H), 4.81-4.73 (m, 1H), 4.44 (s, 2H), 4.36-4.28 (m, 1H), 2.54-2.37 (m, 4H).

With the rapid development of chemical substances, we look forward to future research findings about 100058-61-5.

Reference:
Article; Sheng, Ren; Yang, Liu; Zhang, Yanchun; Xing, Enming; Shi, Rui; Wen, Xiaoan; Wang, Heyao; Sun, Hongbin; Bioorganic and Medicinal Chemistry Letters; vol. 28; 15; (2018); p. 2599 – 2604;,
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In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 100058-61-5, name is 3-(Benzyloxy)cyclobutanol, the common compound, a new synthetic route is introduced below. SDS of cas: 100058-61-5

Step 1: 2-[5-(3-benzyloxycyclobutoxy)-2,2-difluoro-pentoxy]tetrahydropyran To a solution of 3-benzyloxycyclobutanol (2.59 g, 14.53 mmol, 1.10 eq) in N,N-dimethylformamide (100 mL) was added sodium hydride (581 mg, 14.53 mmol, 60% in mineral oil, 1.10 eq) at 0 C. under nitrogen. The mixture was stirred at 0 C. for 0.5 hours and added a solution of (4,4-difluoro-5-tetrahydropyran-2-yloxy-pentyl) 4-methylbenzenesulfonate (5.0 g, 13.21 mmol, 1.00 eq) [prepared as described for Compound 171] in N,N-dimethylformamide (20 mL) dropwise at 0 C. The reaction mixture was stirred at 60 C. for 6 hours. The mixture was cooled to 25 C. and poured into ice-water (w/w=1/1) (30 mL) and stirred for 15 minutes. The aqueous phase was extracted with ethyl acetate (100 mL*3). The combined organic phase was washed with brine (100 mL*3), dried with anhydrous sodium sulfate, filtered and concentrated under vacuum. The residue was purified by silica gel chromatography (Petroleum ether/Ethyl acetate=1/0, 20/1) to afford 2-[5-(3-benzyloxycyclobutoxy)-2,2-difluoro-pentoxy]tetrahydropyran (1.75 g, 4.21 mmol, 32% yield, 92% purity) as a colorless oil.

The synthetic route of 100058-61-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Arvinas, Inc.; Crew, Andrew P.; Berlin, Michael; Flanagan, John J.; Dong, Hanqing; Ishchenko, Alexey; (559 pag.)US2018/125821; (2018); A1;,
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Adding a certain compound to certain chemical reactions, such as: 100058-61-5, 3-(Benzyloxy)cyclobutanol, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, Product Details of 100058-61-5, blongs to alcohols-buliding-blocks compound. Product Details of 100058-61-5

Preparation of 3-(benzyloxy)cyclobutyl sulfochloridate (CC): A solution of compound BB (1.7 g, 9.53 mmol) in DCM (100 ml) was treated with triethylamine (3.34 ml, 23.84 mmol) followed by MeSO2Cl (MsCl) (1.47 ml, 19.07 mmol) and stirred at 25 C. for 30 minutes. The reaction mixture was poured into water and extracted with DCM. The organic layer was dried over Na2SO4, filtered, and concentrated to provide crude CC. Yield: 3.5 g. 1H NMR (400 MHz, CDCl3): 7.36-7.27 (m, 5H), 4.67-4.60 (m, 1H), 4.42 (s, 2H), 3.76-3.69 (m, 1H), 2.97 (s, 3H), 2.85-2.78 (m, 2H), 2.35-2.28 (m, 2H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,100058-61-5, 3-(Benzyloxy)cyclobutanol, and friends who are interested can also refer to it.

Reference:
Patent; Pfizer Inc; US2008/280879; (2008); A1;,
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Adding a certain compound to certain chemical reactions, such as: 100058-61-5, 3-(Benzyloxy)cyclobutanol, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, 100058-61-5, blongs to alcohols-buliding-blocks compound. category: alcohols-buliding-blocks

To a solution of 3-benzyloxycyclobutanol (5.0 g, 28.0 mmol) in dichloromethane (40 mL)was added dropwise diethylaminosulfur trifluoride (7.41 mL, 56.1 mmol) at 0 C. Thereaction was stirred at 15 C for 16 h and quenched with ice water (50 mL). Saturated aqueous sodium bicarbonate was added (100 mL), and the mixture was extracted with dichloromethane (200 mL). The organic phase was washed with brine (100 mL), dried over sodium sulfate and concentrated. The crude product was purified by flash column chromatography (eluting gradient: 10% ethyl acetate in petroleum ether) to give (3- fluorocyclobutoxy)methylbenzene (1.30 g, 26%) as a yellow oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,100058-61-5, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; BRYAN, Marian C.; DO, Steven; DROBNICK, Joy; GOBBI, Alberto; KATSUMOTO, Tamiko; KIEFER, JR., James Richard; LIANG, Jun; RAJAPAKSA, Naomi S.; CHEN, Yongsheng; FU, Liqiang; LAI, Kwong Wah; LIU, Zhiguo; WAI, John; WANG, Fei; (322 pag.)WO2018/234345; (2018); A1;,
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Related Products of 100058-61-5, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 100058-61-5, name is 3-(Benzyloxy)cyclobutanol. A new synthetic method of this compound is introduced below.

To a solution of anti-3-(benzyloxy)cyclobutan-1-ol (3.65 mmol, 650 mg) in dry DMF (8 mL) was added 60% sodium hydride(5.47 mmol, 1.5 equiv.) portion wise at 0 C. After the mixture was stirred at 0 C for 15 min, iodomethane (7.29 mmol, 454 muL) was added dropwise at 0 C. The reaction mixture was stirred at room temperature (~ 25 C) for 1-2 h. The mixture was quenched with saturated aqueous of NH4Cl (10 mL), diluted with water (20 mL), extracted with ethyl acetate (20 mL × 2), washed with brine (20 mL), the organic layer was concentrated under reduced pressure, and the crude product was purified by column chromatography on silica gel (petroleum ether/ethyl acetate = 60:1 as eluent) to give ((anti-3-methoxycyclobutoxy) methyl) benzene (513 mg, 73 % yield) as colorless oil.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,100058-61-5, 3-(Benzyloxy)cyclobutanol, and friends who are interested can also refer to it.

Reference:
Article; Sheng, Ren; Yang, Liu; Zhang, Yanchun; Xing, Enming; Shi, Rui; Wen, Xiaoan; Wang, Heyao; Sun, Hongbin; Bioorganic and Medicinal Chemistry Letters; vol. 28; 15; (2018); p. 2599 – 2604;,
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Application of 100058-61-5 , The common heterocyclic compound, 100058-61-5, name is 3-(Benzyloxy)cyclobutanol, molecular formula is C11H14O2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

In a.solution of 2-(5-bromo-3-ethylsulfonyl-2-pyridyl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridine(1 g, 2.226 mmol) in methylsulfinylmethane (6 mL) were added dipotassium;carbonate (8.905 mmol,1.231 g) and 3-benzyloxycyclobutanol (6.679 mmol, 1.190 g). The reaction vial was placed inmicrowave and heated at 148 oc for 2 hours. After completion of reaction, reaction mixture was poured into water (60ml ), and the aqueous layer was extracted with ethyl acetate. The combinedorganic layer was washed with aqueous saturated sodium chloride solution (30ml), dried overanhydrous sodium sulfate, and concentrated of under reduced pressure. The residue was purify overreduced pressure.LCMS :- rt 1.13 min ,mass 547 (M+1) 1 H NMR (400 MHz, CHLOROFORM-d) d ppm 1.34- 1.38 (m, 3 H) 2.54- 2.81 (m, 3 H) 2.85- 3.03 (m,2 H) 3.03-3.14 (m, 2 H) 3.77-3.83 (m, 2H) 3.87 (s, 3 H) 4.07-4.16 (m, 1 H) 4.88 (quin, J=6.97 Hz, 1H) 7.79-7.84 (m, 1 H) 8.09-8.12 (m, 1 H) 8.57 (d, J=2.81 Hz, 1 H) 8.95-9.00 (m, 1H).

The synthetic route of 100058-61-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; RENDLER, Sebastian; EDMUNDS, Andrew; EMERY, Daniel; JUNG, Pierre, Joseph, Marcel; MUEHLEBACH, Michel; RAWAL, Girish; SEN, Indira; SIKERVAR, Vikas; (110 pag.)WO2018/197315; (2018); A1;,
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Reference of 100058-61-5, Adding some certain compound to certain chemical reactions, such as: 100058-61-5, name is 3-(Benzyloxy)cyclobutanol,molecular formula is C11H14O2, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 100058-61-5.

Step 3: 2-((6-(3-((1r,3r)-3-(benzyloxy)cyclobutoxy)phenoxy)hexyl)oxy)tetrahydro-2H-pyran To a solution of 3-((6-((tetrahydro-2H-pyran-2-yl)oxy)hexyl)oxy)phenol (100 mg, 0.34 mmol), (1s,3s)-3-(benzyloxy)cyclobutanol (91 mg, 0.51 mmol), PPh3 (267 mg, 1.02 mmol) in THF (5.0 mL) were added DIAD (206 mg, 1.02 mmol) at 40 C. under a nitrogen atmosphere. The resulting mixture was heated to 80 C. overnight. After cooling to room temperature, the reaction was quenched with water. The mixture was extracted with EA (50 mL), and the organic phase was washed with water (20 mL*3), brine (20 mL), dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified to afford the desired product (PE:EA=5:1) (130 mg, yield=84%) as colorless oil. 2-((6-(3-((1r,3r)-3-(benzyloxy)cyclobutoxy)phenoxy)hexyl)oxy)tetrahydro-2H-pyran was converted into the final compound, 2-(2,6-dioxopiperidin-3-yl)-5-((6-(3-((1r,3r)-3-((5-(5-methyl-5H-pyrido[4,3-b]indol-7-yl)pyridin-2-yl)oxy)cyclobutoxy)phenoxy)hexyl)oxy)isoindoline-1,3-dione, according to the synthetic scheme below using procedures described above and common procedures known to those skilled in the art. Compound 84: 1H NMR (400 MHz, CDCl3): delta 93.4 (s, 1H), 8.58 (d, J=5.6 Hz, 1H), 8.21-8.48 (m, 2H), 8.20 (d, J=8.4 Hz, 1H), 7.88-7.91 (m, 1H), 7.76 (d, J=8.4 Hz, 1H), 7.56 (s, 1H), 7.51 (d, J=8.0 Hz, 1H), 7.33-7.36 (m, 2H), 7.16-7.18 (m, 2H), 6.86 (d, J=8.4 Hz, 1H), 6.39-6.51 (m, 3H), 5.52-5.54 (m, 1H), 4.94-4.96 (m, 2H), 4.07-4.10 (m, 2H), 3.91-3.97 (m, 5H), 3.22-3.24 (m, 1H), 2.69-2.76 (m, 7H), 2.14-2.16 (m, 1H), 1.82-1.86 (m, 4H), 1.54-1.57 (m, 4H). (M+H)+ 794.5. Synthetic Scheme for Exemplary Compound 86

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 100058-61-5, 3-(Benzyloxy)cyclobutanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Arvinas, Inc.; Crew, Andrew P.; Berlin, Michael; Flanagan, John J.; Dong, Hanqing; Ishchenko, Alexey; (559 pag.)US2018/125821; (2018); A1;,
Alcohol – Wikipedia,
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Synthetic Route of 100058-61-5 ,Some common heterocyclic compound, 100058-61-5, molecular formula is C11H14O2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

To a solution of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine 31-a (392 mg, 2.5 mmol) and Intermediate 31-b (500 mg, 2.8 mmol) in THF (12.7 mL) were sequentially added triphenylphosphine (2.0 g, 7.6 mmol), and DIAD (1.5 ml, 7.6 mmol). The solution was stirred at room temperature for 1 hour. Volatiles were removed under reduced pressure. Purification by silica gel chromatography provided Intermediate 5-c as a beige oil.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 100058-61-5, 3-(Benzyloxy)cyclobutanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PHARMASCIENCE INC.; LAURENT, Alain; ROSE, Yannick; WO2015/77866; (2015); A1;,
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Related Products of 100058-61-5, Adding some certain compound to certain chemical reactions, such as: 100058-61-5, name is 3-(Benzyloxy)cyclobutanol,molecular formula is C11H14O2, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 100058-61-5.

[00278] To a solution of 3-(benzyloxy)cyclobutan-1 -ol (500 mg, 2.8 mmol, cis/trans 85% : 15%), 4-nitrobenzoic acid (935 mg, 5.6 mmol) and PPh3 (2.2 g, 8.4 mmol) in dry THF (25 mL) was added DIAD (1 .7 g, 8.4 mmol) dropwise at 0 C under N2 atmosphere. After addition was completed, the mixture was stirred at 0 C for 15 min and then allowed to room temperature overnight. The mixture was concentrated and then purified by column chromatography on silica gel (PE:EA=10:1) to give the title compound (900 mg, 98%) as a yellow solid. 1H NMR (300 MHz, CDCI3) delta ppm 8.31 – 8.26 (m, 2H), 8.23 – 8.18 (m, 2H), 7.39 – 7.27 (m, 5H), 5.44 (dq, 1 H), 4.47 (d, 2H), 4.37 (tt, 1 H), 2.67 – 2.56 (m, 2H), 2.55 – 2.44 (m, 2H).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 100058-61-5, 3-(Benzyloxy)cyclobutanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NOVARTIS AG; HE, Feng; DU-CUNY, Lei; XIAO, Qitao; XUN, Guoliang; ZHENG, Qiangang; (152 pag.)WO2017/149463; (2017); A1;,
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