Related Products of 637031-88-0, 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.
: 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.
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.; JOSEY, John A.; SHRIMALI, Rajeev; WALLACE, Eli M.; WONG, Tai; (195 pag.)WO2019/191227; (2019); A1;,
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