Sodium borohydride → HCID 59383050, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (S)-methyl 2-(tert-butoxycarbonylamino)-3-(4,4-difluorocyclohexyl)propanoate (28.6 g, 0.089 mol), prepared as described in U.S. Pat. No. 5,688,946, in ethanol (600 mL) at 0° C. was added NaBH4 (27.1 g, 0.713 mol) in portions while the temp. was maintained at 0-5° C. The mixture was stirred for 2-3 h at rt and then evaporated. The residue was partitioned between water and EtOAc. The organic layer was washed with H2O and brine, dried over Na2SO4 and evaporated to give (S)-tert-butyl 1-(4,4-difluorocyclohexyl)-3-hydroxypropan-2-ylcarbamate (25.7 g, 99%), which was used in the next step without purification. 1H NMR (400 MHz, CDCl3): 4.61 (d, J=7.6 Hz, 1H), 3.70 (m, 1H), 3.50 (m, 1H), 2.45-1.10 (m, 11H), 1.44 (s, 9H); MS (E/Z): 295 (M+H+).

Provenance & Evidence