Category: 4415-73-0

Electric Literature of 4415-73-0, 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 4415-73-0, name is 1,1-Cyclobutanedimethanol. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of [1-(hydroxymethyl)-cyclobutyl]methanol (2.50 g, 21.5 mmol, 1.0 equiv.) which was prepared as described in the reference (F. X. Tavares et al., J. Med. Chem. 2004, 47, 5057-5068) in CH2Cl2 (43 mL) was added SOCl2 (2.35 mL, 32.3 mmol, 1.5 equiv.) slowly at 0 C. After being stirred for 2 h at 25 C., the reaction was diluted (10% MeOH/CH2Cl2) and washed (1×H2O and 1×brine). The organic layer was dried (Na2SO4) and concentrated under reduced pressure to provide the product as a colorless liquid

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; Amgen Inc.; US2007/299111; (2007); A1;,
Alcohol – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 4415-73-0, 1,1-Cyclobutanedimethanol, 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, blongs to alcohols-buliding-blocks compound. COA of Formula: C6H12O2

To a solution of cyclobutane-l,l-diyldimethanol (10.00 g, 86.1 mmol) in N,N- dimethylformamide (200 mL), imidazole (8.8 g, 129.1 mmol) and tert-butyldimethylsilyl chloride (12.98 g, 86.1 mmol) were added in one portion at 0 C. The reaction mixture was stirred at 0 C for 10 minutes and then warmed to room temperature for 4 hours. The reaction mixture was quenched with water (500 mL) and extracted with ethyl acetate (250 mL x 3). The combined organic layer was washed with water, brine, dried over MgS04 and concentrated. The resultant residue was purified by flash chromatography (120 g silica gel, 0- 20 % ethyl acetate in hexanes) to get the title compound as a colorless oil. NMR (300 MHz, CDCb): delta 3.71 (s, 1H), 3.69 (d, J= 5.0 Hz, 1H), 2.87 (t, J= 5.4 Hz, 1H), 2.00-1.72 (m, 6H), 0.91 (s, 6H), 0.10 (s, 6H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4415-73-0, its application will become more common.

Reference:
Patent; FGH BIOTECH, INC.; UESUGI, Motonari; KINCAID, John; HUFF, Joel; (150 pag.)WO2018/49080; (2018); A1;,
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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;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

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;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Application of 4415-73-0 ,Some common heterocyclic compound, 4415-73-0, molecular formula is C6H12O2, 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.

Example 134A {1-[(benzyloxy)methyl]cyclobutyl}methanol A solution of cyclobutane-1,1-diyldimethanol (1.04 g, 8.95 mmol) in 1:1 tetrahydrofuran: N,N-dimethylformamide (10 mL) under N2 was treated with 60% dispersion of sodium hydride in mineral oil (0.358 g, 8.95 mmol), stirred at ambient temperature for 2 hours, treated with benzyl bromide (1.065 ml, 8.95 mmol) and stirred at ambient temperature overnight. The mixture was partitioned between methyl tert-butyl ether (50 mL) and saturated NH4Cl solution. The methyl tert-butyl ether layer was washed with water (25 mL) and brine sequentially, dried (MgSO4), filtered, concentrated, and chromatographed on silica gel, eluting with a gradient of 10% to 30% ethyl acetate in heptanes to provide the title compound (0.7 g, 3.39 mmol, 37.9% yield). 1H NMR (500 MHz, CDCl3) delta 7.40-7.30 (m, 5H), 4.56 (s, 2H), 3.72 (d, J=5.6 Hz, 2H), 3.59 (s, 2H), 2.58 (t, J=5.7 Hz, 1H), 2.01-1.78 (m, 6H); MS (DCI) m/z 224 (M+NH4)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4415-73-0, its application will become more common.

Reference:
Patent; AbbVie S.a.r.l.; Galapagos NV; Altenbach, Robert J.; Bogdan, Andrew; Cowart, Marlon D.; Esmieu, William Ramesh; Gfesser, Gregory A.; Greszler, Stephen N.; Koenig, John R.; Kym, Philip R.; Liu, Bo; Malagu, Karine Fabienne; Patel, Sachin V.; Scanio, Marc J.; Searle, Xenia B.; Voight, Eric; Wang, Xeuqing; Yeung, Ming C.; (202 pag.)US2017/15675; (2017); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

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. 4415-73-0, name is 1,1-Cyclobutanedimethanol, the common compound, a new synthetic route is introduced below. Formula: C6H12O2

B. Preparation of cis-1, 2-bis-(bromomethyl) cyclobutane (XXI) To 44 g of phosphorous tribromide (-10 C.) was added dropwise 10.7 g of distilled XX over a 1 hour period. The reaction mixture was warmed to 25 C. and stirred for 2 hours, then heated to 80-85 C. for 18 hours. The reaction mixture was cooled in ice and cold water added. The layers were separated and the aqueous layer was extracted with methylene chloride. The organic extracts were combined, washed with 5% aqueous sodium carbonate and water, then distilled to yield 13.8 g of the title compound XXI as a purple oil, bp 86 (vacuum pump): ir (CHCl3) 3.4, 7.0-8.1mu (no OH signal observed); nmr delta 1.3-2.5 (m, 4), 2.8 (m, 2), and 3.5 (m, 2).

The synthetic route of 4415-73-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Miles Laboratories, Inc.; US4206127; (1980); A;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Application of 4415-73-0, 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.4415-73-0, name is 1,1-Cyclobutanedimethanol, molecular formula is C6H12O2, molecular weight is 116.1583, as common compound, the synthetic route is as follows.

Step 2:Oxalyl chloride (61.5 ml_, 708 mmol) is added over 1.5 h to a -80 C (internal temperature; Et20/dry-ice bath is used for cooling) solution of DMSO (50.2 ml_, 708 mmol) in DCM (3.00 L). The reaction mixture is allowed to stir at -80 C for 0.5 h, and then a solution of 4a1 (30.9 g, 266 mmol) in DCM (500 mL) is added over 1 h while maintaining an internal temperature of -80 C. The reaction mixture is stirred for 0.5 h at -80 C, and then TEA (297 mL, 2.13 mol) is added over 1 h while keeping an internal temperature of -80 C. The cooling bath is removed, and the reaction mixture is allowed to warm to 10 C over 4 h. The crude material containing 4a2 is used as such in the next step.

Statistics shows that 4415-73-0 is playing an increasingly important role. we look forward to future research findings about 1,1-Cyclobutanedimethanol.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BROCHU, Christian; GRAND-MAITRE, Chantal; FADER, Lee; KUHN, Cyrille; BERTRAND-LAPERLE, Megan; PESANT, Marc; WO2013/26163; (2013); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Synthetic Route 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.

Add 2.6 ml of an 11.25N sodium hydroxide solution at 70 C. to a solution of 1.72 g (14.85 mmol) of cyclobutane-1,1-diyldimethanol [F. X. Tavares, J. Med. Chem. 2004, 47 (21), 5057-5068] in 20 ml of toluene, 8 ml of 1,2-dimethoxyethane and 8 ml of water. After adding 0.10 g (0.30 mmol) of tetra-n-butylammonium hydrogen sulphate and 1.00 g (2.97 mmol) of 4-chloro-5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidine, stir the reaction mixture at 70 C. for 17 h. After cooling to room temperature, adjust to pH 7 with concentrated hydrochloric acid. Extract three times with 50 ml of dichloromethane each time. Wash the combined organic extracts with satd. sodium chloride solution, dry over sodium sulphate and filter. Concentrate the filtrate under reduced pressure. Stir the residue in acetonitrile, filter and purify the filtrate by means of preparative RP-HPLC (gradient: water/acetonitrile). 0.30 g (24% of theory) of the desired product are obtained. LC-MS (Method 3): Rt=2.67 min; m/z=417 (M+H)+ 1H-NMR (400 MHz, DMSO-d6): delta=8.58 (s, 1H), 7.56-7.54 (m, 2H), 7.42-7.37 (m, 5H), 7.04-6.99 (m, 2H), 4.56 (t, 1H), 4.30 (s, 2H), 3.81 (s, 3H), 3.21 (d, 2H), 1.77-1.58 (m, 6H).

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; BAYER SCHERING PHARMA AKTIENGESELLSCHAFT; US2011/124665; (2011); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts