Category: 637031-88-0

Adding a certain compound to certain chemical reactions, such as: 637031-88-0, 3,3-Difluorocyclobutanol, 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, 637031-88-0, blongs to alcohols-buliding-blocks compound. Product Details of 637031-88-0

To a mixture of A-102 (180 mg, 0.61 mmol), 3,3-difluorocyclobutanol (98.5 mg, 0.91 mmol) and PPh3 (286.81 mg, 1.09 mmol) in THF (3 mL) was added DEAD (190.43 mg, 1.09 mmol) at 0 C. The mixture was allowed to warm and then was stirred at 70 C for 16 hours. After cooling to room temperature, the mixture was concentrated to give the crude product, which was purified by prep-TLC (silica gel, PE: EtOAc = 3:1) and prep-HPLC (Phenomenex Gemini (250 mm x 50 mm, 10 _); A = H20 (0.05% NH4OH) and B = CH3CN; 48-78% B over 8 minutes) to afford Compound 81 (5.08 mg, 0.01 mmol) as a solid. 1H NMR (400MHz, CDC13) _ = 9.57 (d, 1H), 8.34 (s, 1H), 7.93 (d, 2H), 6.97 (d, 2H), 4.83 -4.65 (m, 1H), 3.23 – 3.06 (m, 2H), 2.91 -2.75 (m, 2H). LCMS R, = 1.19 min using Method A, MS ESI calcd. for Ci6H12F5N40 [M+H]+ 371.1, found 371.0.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,637031-88-0, its application will become more common.

Reference:
Patent; PRAXIS PRECISION MEDICINES, INC.; REDDY, Kiran; MARTINEZ BOTELLA, Gabriel; GRIFFIN, Andrew, Mark; MARRON, Brian, Edward; (364 pag.)WO2018/98499; (2018); A1;,
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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. 637031-88-0, name is 3,3-Difluorocyclobutanol. A new synthetic method of this compound is introduced below., COA of Formula: C4H6F2O

: A solution of 4′-bromo-6′- fluoro-r-(trifluoromethyl)spiro[l,3-dioxolane-2,7′-5,6-dihydrocyclopenta[c]pyridine] (0809) (96.2mg, 0.2800mmol) and 2-(di-t-butylphosphino)-3,6-dimethoxy-2′,4′,6′-tri-i-propyl-l,r- biphenyl (3.4 mg, 0.007 mmol) in l,4-dioxane (5.0 mL) was sparged with nitrogen for 3 mins. The reaction mixture was then treated sequentially with potassium hydroxide (47.3 mg, 0.84 mmol), water (101 pL, 5.62 mmol) and [2-(2-aminophenyl)phenyl]-methylsulfonyloxy- palladium; di-t-butyl-[3,6-dimethoxy-2-(2,4,6-triisopropylphenyl)phenyl]phosphane (6.0 mg, 0.007 mmol) under continuous nitrogen stream. The vessel was sealed and heated to 80 C for 1 h and 30 min. The reaction mixture was quenched by the addition of acetic acid (64.3 pL, 1.13 mmol). The reaction mixture was poured into 75 mL of water and extracted with 4 x 20 mL EtOAc. The combined organics were dried with MgS04, filtered, and concentrated to dryness. The product was used without further purification (87 mg). During the reaction, some of the hydrodefluorinated product formed as an impurity. Data for 6-fluoro-l- (trifluoromethyl)-5,6-dihydrospiro[cyclopenta[c]pyridine-7,2′-[l,3]dioxolan]-4-ol: LCMS ESI (+) (M+H) m/z 280. Data for l-(trifluoromethyl)-5,6- dihydrospiro[cyclopenta[c]pyridine-7,2′-[l,3]dioxolan]-4-ol: LCMS ESI (+) (M+H) m/z 262.A solution of impure 6′-fluoro-r-(trifluoromethyl)spiro[l,3-dioxolane-2,7′- 5,6-dihydrocyclopenta[c]pyridine]-4′-ol (44.0 mg, 0.16 mmol), polymer supported (0812) triphenylphosphine (-2.06 mmol/g, 306.2 mg, 0.63 mmol), and 3,3-difluoro-cyclobutanol (68.1 mg, 0.63 mmol) in tetrahydrofuran (3.2 mL) was treated with diisopropyl (0813) azodicarboxylate (120 pL, 0.61 mmol) and stirred at 60 C for 2 h. The reaction mixture was filtered and the filter cake rinsed with 20 mL EtOAc. The filtrate was concentrated and purified by chromatography on silica using 10-30% EtO Ac/hexane to afford a clear solid (39.0 mg, 67%) that was a 2: 1 mixture of the fluorinated and hydrodefluorinated products. LCMS ESI (+) (M+H) m/z 370. Data for 4-(3,3-difluorocyclobutoxy)-6-fluoro-l- (trifluoromethyl)-5,6-dihydrospiro[cyclopenta[c]pyridine-7,2′-[l,3]dioxolane]: LCMS ESI (+) (M+H) m/z 370. Data for 4-(3,3-difluorocyclobutoxy)-l-(trifluoromethyl)-5,6- dihydrospiro[cyclopenta[c]pyridine-7,2′-[l,3]dioxolane]: LCMS ESI (+) (M+H) m/z 352.A solution of impure 4′-(3,3-difluorocyclobutoxy)-6′-fluoro-r-(trifluoromethyl)spiro[l,3- dioxolane-2,7′-5,6-dihydrocyclopenta[c]pyridine] (39.0 mg, 0.106 mmol) in dichloromethane (2.0 mL) at 0 C was treated with perchloric acid (70% in water, 200 pL) and stirred at 0 C for 3 h. The reaction mixture was quenched by the addition of 5 mL of saturated aqueous (0817) NaHC03. The resulting mixture was extracted with 3 x 15 mL CH2Cl2. The combined organics were rinsed with 10 mL of brine, dried with MgS04, filtered, and concentrated to dryness. The product was used without further purification as a 2: 1 mixture of fluorinated and hydrodefluorinated ketones. LCMS ESI (+) (M+H) m/z 326. Data for 4-(3,3- difluorocyclobutoxy)-6-fluoro-l-(trifluoromethyl)-5,6-dihydro-7iT-cyclopenta[c]pyridin-7- one: LCMS ESI (+) (M+H) m/z 326. Data for 4-(3,3-difluorocyclobutoxy)-l- (trifluoromethyl)-5,6-dihydro-7i7-cyclopenta[c]pyridin-7-one: LCMS ESI (+) (M+H) m/z 308.A solution of impure 4-(3,3-difluorocyclobutoxy)-6-fluoro-l- (trifluoromethyl)-5,6-dihydrocyclopenta[c]pyridin-7-one (33.8 mg, 0.10 mmol) in dichloromethane (4.0 mL) was cooled to 0 C and sparged with nitrogen for 5 min. During this time formic acid (11.8 pL, 0.31 mmol) and triethylamine (28.8 pL, 0.21 mmol) were sequentially added. Once sparging was complete, RuCl(p-cymene)[(R,R)-Ts-DPEN] (1.3 mg, 0.002 mmol) was added under a continuous stream of nitrogen. The reaction vessel was sealed and placed into the refrigerator to react overnight. Volatiles were removed by concentration under reduced pressure. The residue was purified by chromatography on silica using 4-18% EtOAc/CH2Cl2 to afford ( 6R, 7L’)-4-(3 , 3 -difl uorocy d obutoxy )-6-fl uoro- 1 – (trifluoromethyl)-6,7-dihydro-5iT-cyclopenta[c]pyridin-7-ol (Compound 465) as a clear solid (5.4 mg, 16%) and (f?)-4-(3,3-difluorocyclobutoxy)-l-(trifluoromethyl)-6,7-dihydro-5i7- cyclopenta[c]pyridin-7-ol (Compound 466) as a clear solid (7.4 mg, 23%). Data for ( 6R,7S )- 4-(3, 3 -difl uorocycl obutoxy )-6-fluoro- l -(trifluoromethyl)-6,7-dihydro-5//- cyclopenta[c]pyridin-7-ol (Compound 465): Retention time HPLC (14 min) = 3.59 min; LCMS ESI (+) (M+H) m/z 328; 1H NMR (400 MHz, CDCl3): d 8.04 (s, 1H), 5.46-5.26 (m, 2H), 4.89-4.79 (m, 1H), 3.36-3.08 (m, 4H), 2.91-2.74 (m, 2H), 2.60 (dd, 1H). Data for (i?)-4-(3,3-difluorocyclobutoxy)-l-(trifluoromethyl)-6,7-dihydro-5iT-cyclopenta[c]pyridin-7- ol (Compound 466): Retention time HPLC (14 min) = 3.95 min; LCMS ESI (+) (M+H) m/z 310; 1H NMR (400 MHz, CDCI3): d 7.98 (s, 1H), 5.59-5.54 (m, 1H), 4.88-4.79 (m, 1H), 3.24- 3.07 (m, 3H), 2.89 (dd, 1H), 2.89-2.74 (m, 2H), 2.44-2.34 (m,…

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 637031-88-0, 3,3-Difluorocyclobutanol.

Reference:
Patent; PELOTON THERAPEUTICS, INC.; JOSEY, John A.; SHRIMALI, Rajeev; WALLACE, Eli M.; WONG, Tai; (195 pag.)WO2019/191227; (2019); A1;,
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Application of 637031-88-0, 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. 637031-88-0, name is 3,3-Difluorocyclobutanol, molecular formula is C4H6F2O, 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 7′-methylsulfonylspiro[l,3- dioxolane-2,l’-indane]-4′-ol (2.0 g, 7.4 mmol), triphenylphosphine (8.2 g, 31.1 mmol), and 3,3-difluoro-cyclobutanol (1.04 g, 9.6 mmol) in tetrahydrofuran (50 mL) at 60 C was added diisopropyl azodicarboxylate (2.3 mL, 11.8 mmol). After addition, the reaction mixture was stirred at 60 C overnight. After cooled to ambient temperature, water (50 mL) and MTBE (50 mL) were added. The organic layer was separated, washed with brine, dried (sodium sulfate), filtered and concentrated under reduced pressure. The residue obtained was purified by flash chromatography on silica gel to give 4′-(3,3-difluorocyclobutoxy)-7′-methylsulfonyl- spiro[l,3-dioxolane-2,l’-indane] (1.0 g, 37%) as solid.

According to the analysis of related databases, 637031-88-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PELOTON THERAPEUTICS, INC.; DIXON, Darryl, David; GRINA, Jonas; JOSEY, John, A.; RIZZI, James, P.; SCHLACHTER, Stephen, T.; WALLACE, Eli, M.; WANG, Bin; WEHN, Paul; XU, Rui; YANG, Hanbiao; (237 pag.)WO2016/144825; (2016); A1;,
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Related Products of 637031-88-0 ,Some common heterocyclic compound, 637031-88-0, molecular formula is C4H6F2O, 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.

A solution of racemic-2′,3′,4′- trifluoro-7′-methylsulfonyl-spiro[l,3-dioxolane-2, -indane] (19.3 mg, 0.063 mmol) and 3,3- difluoro-cyclobutanol (9.8 muEpsilon, 0.10 mmol) in acetonitrile (1.0 mL) at 25 C was treated with potassium hydroxide (5.3 mg, 0.094 mmol) and stirred at 25 C for 1 h. An additional portion of potassium hydroxide (5.3 mg, 0.094 mmol) was added to drive the reaction to completion. Volatiles were removed by concentration under reduced pressure. The reaction mixture was poured into 20 mL of water and extracted with 3 x 20 mL EtOAc. The combined organics were rinsed with 10 mL of brine, dried with MgS04, filtered, and concentrated to dryness. An off-white solid (27.2 mg) was isolated and used without further purification. LCMS ESI (+) [M+H]+ m/z 397.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,637031-88-0, its application will become more common.

Reference:
Patent; PELOTON THERAPEUTICS, INC.; DIXON, Darryl, David; GRINA, Jonas; JOSEY, John, A.; RIZZI, James, P.; SCHLACHTER, Stephen, T.; WALLACE, Eli, M.; WANG, Bin; WEHN, Paul; XU, Rui; YANG, Hanbiao; (237 pag.)WO2016/144825; (2016); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts