Sodium borohydride → HCID 68015104, compound

Participants

Reaction Steps

To a solution of (2R,3S,4S,5R,6S)-3,4,5-tribenzyloxy-6-[4-chloro-3-[(4-ethoxy-2,3-difluoro-phenyl) methyl]phenyl]-2-(hydroxymethyl)-6-methoxy-tetrahydropyran-2-carbaldehyde 23l (3.30 g, 4.31 mmol) in methanol (60 mL) was added sodium borohydride (326 mg, 8.62 mmol) at 0° C. The mixture was warmed up to room temperature and stirred for 30 min. The reaction mixture was quenched with saturated aqueous ammonium chloride (15 mL), and then water (20 mL) was added. The mixture was extracted with ethyl acetate (30 mL×3). The combined organic layers were dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to give the title compound 23m as yellow oil (3.41 g, 100%). This material was not further purified. The compound was characterized by the following spectroscopic data: 1H NMR (400 MHz, DMSO-d6) δ(ppm): 7.57 (m, 1H), 7.45 (m, 2H), 7.28 (m, 13H), 7.03 (m, 2H), 6.78 (t, 1H), 6.60 (t, 1H), 4.87 (s, 1H), 4.79 (m, 3H), 4.68 (d, 1H), 4.51 (d, 1H), 4.39 (s, 1H), 4.06 (m, 5H), 3.93 (t, 3H), 3.77 (m, 2H), 3.52 (d, 1H), 3.18 (d, 1H), 3.09 (s, 3H), 1.32 (t, 3H).

Provenance & Evidence