Sodium borohydride → HCID 10473616, compound

Participants

Reaction Steps

To a solution of 1-(methyl{4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)-ethyl]phenyl}amino)-pentan-2-one (52 mg, 0.15 mmol) in methanol (3 mL) at −78° C. was added sodium borohydride (17 mg, 0.44 mmol). The reaction mixture was allowed to warm to ambient temperature over 4 hours. The reaction mixture was quenched with water and extracted twice with EtOAc. The combined organic layers were washed with brine, dried (Na2SO4), filtered and concentrated. Purification by flash chromatography (4:1 hexanes/EtOAc) afforded the title compound as a colorless oil (40 mg, 74%). 1H NMR (CDCl3) δ 7.51 (d, 2H), 6.80 (d, 2H), 3.96 (m, 1H), 3.32 (s, 1H), 3.30 (dq, 2H), 3.03 (s, 3H), 1.39-1.52 (m, 4H), 0.96 (t, 3H). 13C NMR (CDCl3) δ 151.0, 127.4, 116.8, 112.1, 69.4, 60.0, 39.3, 36.8, 18.9, 14.1. MS (ES+) m/z 360 (MH+).

Provenance & Evidence