New learning discoveries about 14774-36-8

14774-36-8 (Tetrahydropyran-3-yl)methanol 85769, aTetrahydropyrans compound, is more and more widely used in various fields.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.14774-36-8,(Tetrahydropyran-3-yl)methanol,as a common compound, the synthetic route is as follows.

14774-36-8, To a solution of Compound 29 (100 mg, 0.34 mmol) in THF (4 mL) was added (0759) tetrahydropyran-3-ylmethanol (117.65 mg, 1.01 mmol), PPli3 (177.1 mg, 0.68 mmol) and then DIAD (136.54 mg, 0.68 mmol). The resulting mixture was stirred at 20 C under N2 for 16 hours . The reaction solution was concentrated to give the crude product, which was purified by flash chromatography on silica gel (EtOAc in PE = 0% to 10% to 20%) and Prep- TLC (silica gel, PE: EtOAc = 4: 1) to afford A-58 (50 mg) as a solid. A-58 was purified by SFC (Chiralcel AD (250 mm x 30 mm, 5 muiotaeta); A = C02 and B = EtOH (0.1% NH3H20); 38C; 50 mL/min; 30% B over 11 minutes; multiple injections) to afford Enantiomer 1, randomly assigned as Compound 66 (Rt = 6.8 min) and Enantiomer 2, randomly assigned as Compound 67 (Rt = 9.2 min). Compound 66 (14.37 mg, 0.04 mmol) 1H NMR (CDCI3 400MHz) deltaEta = 8.00 (d, 2H), 7.48 (s, 2H), 7.33 (d, 2H), 4.01 – 3.80 (m, 4H), 3.56 – 3.35 (m, 2H), 2.43 – 2.30 (m, 1H), 1.96 – 1.85 (m, 1H), 1.82 – 1.72 (m, 1H), 1.69 – 1.59 (m, 1H), 1.49 – 1.37 (m, 1H). LCMS Rt = 1.32 min using Method A, MS ESI calcd. for Ci9Hi8F3N204 (0760) [M+H]+ 395.1, found 395.0. Compound 67 (15.66 mg, 0.04 mmol) 1H NMR (CDC13, 400MHz) deltaEta = 8.00 (d, 2H), 7.48 (s, 2H), 7.33 (d, 2H), 4.00 – 3.81 (m, 4H), 3.55 – 3.46 (m, 1H), 3.41 (dd, 1H), 2.43 – 2.31 (m, 1H), 1.96 – 1.86 (m, 1H), 1.82 – 1.72 (m, 1H), 1.69 – 1.59 (m, 1H), 1.49 – 1.37 (m, 1H). LCMS Rt = 1.33 min using Method A, MS ESI calcd. for Ci9Hi8F3N204 [M+H]+ 395.1, found 395.1.

14774-36-8 (Tetrahydropyran-3-yl)methanol 85769, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; PRAXIS PRECISION MEDICINES , INC.; REDDY, Kiran; MARTINEZ BOTELLA, Gabriel; GRIFFIN, Andrew, Mark; MARRON, Brian, Edward; (244 pag.)WO2018/148745; (2018); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics