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
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