Month: August 2021

Related Products of 4415-73-0, Adding some certain compound to certain chemical reactions, such as: 4415-73-0, name is 1,1-Cyclobutanedimethanol,molecular formula is C6H12O2, 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 4415-73-0.

EXAMPLE 41 1-[[[Dimethyl(1,1-dimethylethyl)silyl]oxy]methyl]cyclobutane methanol A solution of 9.9 g (85 mmol) of the compound, presented according to Example 40, in 100 ml of absolute tetrahydrofuran is added at 0 C. to a suspension of 3.4 g of sodium hydride (60% in oil) in 35 ml of absolute tetrahydrofuran. It is allowed to stir for 30 more minutes, and then a solution of 12.8 g of tert-butyldimethylsilyl chloride in 50 ml of tetrahydrofuran is added. It is allowed to stir for one more hour at 25 C., and then the reaction mixture is poured onto saturated aqueous sodium bicarbonate solution. It is extracted with ethyl acetate. The organic phase is washed with saturated sodium chloride solution and dried on sodium sulfate. After the solvent is drawn off in a vacuum, the crude product that is obtained is purified by column chromatography on silica gel with a mixture that consists of hexane/ethyl acetate. 13.5 g (58.6 mmol, 69%) of the title compound is obtained. 1H-NMR (CDCl3): delta=0.04 (6H), 0.90 (9H), 1.70-2.00 (6H), 3.70 (4H) ppm. A solution of 9.9 g of Ca) (85 mmol) in 100 ml of absolute tetrahydrofuran is added at 0 C. to a suspension of 3.4 g of sodium hydride (60% in oil, 85 mmol)) in 35 ml of absolute tetrahydrofuran. It is allowed to stir for 30 more minutes, and then a solution of 12.8 g of tert-butyldimethylsilyl chloride (85 mmol) in 50 ml of tetrahydrofuran is added. It is allowed to stir for one more hour at 25 C., and then the reaction mixture is poured onto saturated aqueous sodium bicarbonate solution. It is extracted with ethyl acetate. The organic phase is washed with saturated sodium chloride solution and dried on sodium sulfate. After the solvent is drawn off in a vacuum, the crude product that is obtained is purified by column chromatography on silica gel with a mixture that consists of hexane/ethyl acetate. 13.5 g (69%) of the title compound is obtained.1H-NMR (CDCl3): delta=0.04 (6H), 0.90 (9H), 1.70-2.00 (6H) 3.70 (4H) ppm.

According to the analysis of related databases, 4415-73-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Schering, AG; US7001916; (2006); B1;,
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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.18776-12-0, name is 3-Chloro-1-phenylpropan-1-ol, molecular formula is C9H11ClO, molecular weight is 170.64, as common compound, the synthetic route is as follows.Quality Control of 3-Chloro-1-phenylpropan-1-ol

General procedure: To starting material 9 or 10, respectively (1 mmol) was added 48% aqueous HBr (3 mL) and the mixture was stirred for 3h at room temperature. Thereafter, the solution was poured into a mixture of K2CO3 (1 g) in ice (5.5 g) and additional solid K2CO3 was added for neutralization (pH 7). The crude reaction product was extracted with diethyl ether, the combined organic layers were dried with MgSO4 and evaporated to dryness. The crude product was employed directly in the subsequent reaction step without further purification.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,18776-12-0, 3-Chloro-1-phenylpropan-1-ol, and friends who are interested can also refer to it.

Reference:
Article; Neudorfer, Catharina; Seddik, Amir; Shanab, Karem; Jurik, Andreas; Rami-Mark, Christina; Holzer, Wolfgang; Ecker, Gerhard; Mitterhauser, Markus; Wadsak, Wolfgang; Spreitzer, Helmut; Molecules; vol. 20; 1; (2015); p. 1712 – 1730;,
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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.1117-86-8, name is 1,2-Octanediol, molecular formula is C8H18O2, molecular weight is 146.23, as common compound, the synthetic route is as follows.category: alcohols-buliding-blocks

General procedure: The reactions were performed in a 50 ml autoclave with a Teflon vessel inside equipped with magnetic stirring under 3.0 MPa CO2. After introducing DBU (60.8 mg, 0.4 mmol), propylene glycol (76.1 mg, 1 mmol), 2-methyl-3-butyn-2-ol (126.2 mg, 1.5 mmol), DMF (2 ml), the autoclave was sealed and filled with CO2 to keep thepressure of CO2 under 3.0 MPa. Then, the reaction mixture was stirred at 120 C for 10 h. When the reaction completed, the autoclave was cooled to ambient temperature and residual CO2 was carefully released. Subsequently, the mixture was flushed with DMF and analyzed by GC using biphenyl as an internal standard.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1117-86-8, 1,2-Octanediol, and friends who are interested can also refer to it.

Reference:
Article; Han, Li-Hua; Li, Jing-Yuan; Song, Qing-Wen; Zhang, Kan; Zhang, Qian-Xia; Sun, Xiao-Fang; Liu, Ping; Chinese Chemical Letters; vol. 31; 2; (2020); p. 341 – 344;,
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Reference of 616-29-5, Adding some certain compound to certain chemical reactions, such as: 616-29-5, name is 1,3-Diaminopropan-2-ol,molecular formula is C3H10N2O, 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 616-29-5.

1,3-diaminopropan-2-ol (3 g, 0.033 mol) was dissolved in methanol (300 ml) followed by the addition of triethylamine (33 ml dropwise) and di-tert-butyl dicarbonate [(BOC)2O] (21.793 g, 0.100 mol). The reaction medium was heated at 40-50 C. for 20 min then stirred at room temperature for 1 hour. After evaporation of the solvent, the colorless oil residue was purified by chromatography on silica gel (eluent: dichloromethane/methanol 95:5). The reaction yielded a colorless oil which crystallized slowly. Yield: quantitative Rf (dichloromethane/methanol 95:5): 0.70 IR: nuNH 3368 cm-1; nuCO carbamate 1690 cm-1 MP: 98-100 C. NMR (1H, CDCl3): 1.45 (multiplet, 18H, -CH3- (BOC)); 3.02 (sl, 1H, OH); 3.15-3.29 (multiplet, 4H, BOCNH-CH2-CH-CH2-NHBOC); 3.75 (m, 1H, BOCNH-CH2-CH-CH2-NHBOC); 5.16 (multiplet, 2H, -NHBOC). MS (MALDI-TOF): M+1=291 (M+H+); M+23=313 (M+Na+); M+39=329 (M+K+)

According to the analysis of related databases, 616-29-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Darteil, Raphael; Caumont-Bertrand, Karine; Najib, Jamila; US2006/69156; (2006); A1;,
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Synthetic Route of 7397-62-8, 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 7397-62-8, name is Butyl 2-hydroxyacetate. This compound has unique chemical properties. The synthetic route is as follows.

The esterification of metharylic acid with BG was done by carbonyl diimidazole coupling. 1 Eq. of methacrylic acid was charged into suitable sized round bottom flask (RBF) with a stir bar. 10 volumes of dichloromethane was then added to it. RBF was then sealed with a rubber septa and the mixture of methacrylic acid and dichloromethane was then flushed with N2 for 5 minutes. The RBF was then placed in an ice bath until the contents cooled down to 0C. Then CDI was then added to the reaction through the mouth of the RBF by removing the septa. Frothing was observed in the reactor. Once the frothing stopped, the reaction vessel was sealed by rubber septa and butyl glycolate was added using a syringe. The ice bath was removed and the reaction allowed to run at room temperature. It was followed by thin layer chromatography (TLC) on silica using 2% isopropanol/98% chloroform and separately using chloroform/methanol/acetic acid (CMA) 98: 2:2. No spot for carbonyl diimidazole was observed after 2.5 hrs. The spot for the compound overlaps with that of carbonyl diimidazole in the TLC done using 2% isopropanol, but a distinct spot was seen for the compound in the TLC done with CMA. Once the reaction was complete, the solvent was removed in vacuo and the sample was purified by column chromatography. The yield was approximately 20%.

According to the analysis of related databases, 7397-62-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; THE UNIVERSITY OF UTAH RESEARCH FOUNDATION; WO2005/97210; (2005); A1;,
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Electric Literature of 505-10-2, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 505-10-2 as follows.

24 g of PBr3 are mixed at 0 C., with stirring, with 20 g of 3-(methylsulphanyl)-1-propanol. The medium is allowed to return to AT and then it is heated at 100 C. for 1 hour. It is allowed to cool to AT and then it is cooled in an ice bath. The medium is taken up in benzene and then is extracted with toluene. The extract is washed with a 1% Na2CO3 solution, with water and then with a saturated NaCl solution. It is dried over MgSO4 and concentrated, and then distillation is carried out to produce 3.6 g of the expected compound.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,505-10-2, its application will become more common.

Reference:
Patent; Barth, Francis; Congy, Christian; Guillaumont, Carole; Rinaldi, Murielle; Vasse, Fabienne; Vernhet, Claude; US2004/34090; (2004); A1;,
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Synthetic Route of 4541-15-5, Adding some certain compound to certain chemical reactions, such as: 4541-15-5, name is 5-(Benzyloxy)pentan-1-ol,molecular formula is C12H18O2, 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 4541-15-5.

00193] 5-Benzyloxy-pentanoic acid (29)[00194] Jones reagent was added dropwise to an ice cooled solution of 5-benzyloxy-pentan- 1 – ol 28 (5 g, 25.74 mmol) in acetone (170 ml). Addition of the Jones reagent was stopped when the acetone solution acquired a persistent yellow color with the concurrent formation of green chromium salts. The mixture was filtered and concentrated in vacuo to give an oily crude product that was purified by a flash chromatography (EtOAc / hexanes, 1 :3) to give compound 29 (4.98 g, 93%) as a colorless oil: TLC R/= 0.68 (silica gel, 50% EtOAc / hexanes); 1HNMR (400 MHz, CDCl3) delta 7.35-7.31 (m, 5H), 4.502 (s, 2H), 3.51-3.47 (t,3J= 6 Hz, 2H), 2.41-2.36 (t, 3J= 6.8 Hz, 2H), 1.79-1.64 (m, 4H); 13C NMR (75 MHz, CDCl3) 5179.713, 138.651, 128.609, 127.870, 127.795, 73.158, 69.968, 33.915, 29.243, 21.749; HRMS calcd for C12H16O3 + Na+ 231.0997; found 231.0992 [M + Na+].

According to the analysis of related databases, 4541-15-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; UNIVERSITY OF TOLEDO; WO2007/15929; (2007); A2;,
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Reference of 27489-62-9 , The common heterocyclic compound, 27489-62-9, name is trans-4-Aminocyclohexanol, molecular formula is C6H13NO, 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.

General procedure: A solution of the desired intermediate 3a-l (0.07 mmol, 1 eq) in 1 mL DMSO was taken in a 5mL sealed reaction vessel, the corresponding amine (trans-4-aminocyclohexanol for 4a-k) (0.212 mmol, 3 eq) then diisopropylethylamine (DIPEA)(0.2l2 mmol, 3eq) was introduced. The reaction vessel was then sealed and heated to 140 C for 12 h, cooled and water (25 mL) was added. The aqueous layer was extracted with ethyl acetate (25 mL X 3), the organic fractions were combined and washed with brine (25mL) and dried over sodium sulfate. Purification with column chromatography (S1O2, 4:96 methanokDCM for 4a-k, 5a,5b,5e and 5: 1 :94 methanol :7M NH3 in methanokDCM for 5c,5d,5f,5g) resulted in the desired products which were further purified by preparative TLC to give the desired compounds 4a-k, 5a-g as light yellow solids. 8-(((lr,4r)-4-hydroxycyclohexyl)amino)-3-methyl-6-(3,6,6-trimethyl-4-oxo- 4,5,6,7-tetrahydro-lH-indazol-l-yl)isoquinolin-l(2H)-one (4a): 22 mg, Yield 70%; NMR (400 MHz, Chloroform -if) d 9.16 (d, J= 7.5 Hz, 1H), 9.05 (s, 1H), 6.51 – 6.40 (m, 2H), 6.09 (s, 1H), 3.74 – 3.59 (m, 2H), 3.31 (d, j= 24.2 Hz, 1H), 2.78 (s, 2H), 2.49 (s, 3H), 2.34 (s, 2H), 2.19 (s, 3H), 2.17 – 2.08 (m, 2H), 2.04 – 1.95 (m, 2H), 1.38 (q, 7= 11.1, 9.9 Hz, 4H), 1.04 (s, 6H). 13C NMR (101 MHz, CDCh) d 193.4, 185.3, 169.7, 165.5, 151.4, 150.0, 149.1, 143.5, 143.2, 142.1, 137.4, 107.3, 105.7, 104.8, 100.3, 69.7, 52.4, 50.2, 37.8, 35.8, 33.5, 29.9, 28.4 (2), 19.0, 13.4. HRMS (ESI) m/z [M+H] calculated for C26H33N4O3, 449.2553, found 449.2566.

The synthetic route of 27489-62-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITY OF NOTRE DAME DU LAC; BLAGG, Brian; SANKET, Mishra; (0 pag.)WO2019/232223; (2019); A1;,
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Synthetic Route of 4704-94-3, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 4704-94-3 as follows.

(10a) 1,5,9-trioxaspiro[5.5]undec-3-ylmethanol A mixture of 2-(hydroxymethyl)-1,3-propanediol (3.3 g, 31.1 mmol), tetrahydro-4H-pyran-4-one (3.12 g, 31.2 mmol), p-toluenesulfonic acid monohydrate (268 mg, 1.41 mmol) and benzene (68.3 ml) was refluxed in a round bottom flask equipped with a cooling tube and Dean-Stark for 6 hours. After cooled to room temperature, triethylamine (1 ml) was added to the reaction mixture and the mixture was concentrated. The residue was purified by silica gel column chromatography (silica gel: 200 g, elution solvent: heptane, heptane/ethyl acetate=1/1, 1/3) to obtain the title compound (3.80 g, yield: 64.9%) as a colorless oil. 1H NMR(400 MHz, DMSO-d6) deltappm; 1.67-1.82(5H, m), 3.35-3.42(2H, m), 3.49-3.57(4H, m), 3.65(2H, dd, J=7, 12 Hz), 3.86(2H, dd, J=4, 12 Hz), 4.56(1H, t, J=5 Hz).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4704-94-3, its application will become more common.

Reference:
Patent; Eisai Co., Ltd.; US2007/10542; (2007); A1;,
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Related Products of 6850-65-3, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 6850-65-3, name is 4-Aminocyclohexan-1-ol(isomers mixture), molecular formula is C6H13NO, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

To a solution of 4-aminocyclohexanol (23 g,0.2 mol) and Et3N (60 g, 0.6 mol) in THF (230 mL) was added (Boc)20 (87 g, 0.4 mol). The resulting solution was stirred at room temperature overnight. The solvent was removed under reduced pressure and the residue was extracted with EtOAc (3 x 200 mL). The combined organic layers were washed with water (2 x 200 mL) and brine (200 mL), dried over anhydrous Na2SO4 and concentrated. The residue was purified by column chromatography on silica gel using DCMI MeOH (V:V, 20:1) to afford the desired product as a white solid. MS: 216.2 (M+1).

According to the analysis of related databases, 6850-65-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AGIOS PHARMACEUTICALS, INC.; LEMIEUX, Rene M.; POPOVICI-MULLER, Janeta; TRAVINS, Jeremy M.; CAI, Zhenwei; CUI, Dawei; ZHOU, Ding; WO2015/10626; (2015); A1;,
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