Sodium borohydride → N-[(1R)-1-[4-(1-Hydroxyethyl)phenyl]ethyl]methanesulfonamide

Participants

Reaction Steps

Dissolve N-[(1R)-1-(4-acetylphenyl)ethyl]methanesulfonamide (15 g, 62 mmol) in EtOH (155.4 mL) and cool with an ice bath. Add sodium borohydride (1.2 g, 31.1 mmol) and stir the resulting mixture in the ice bath for 2 h. Quench the reaction with H2O (20 mL) and concentrate under reduced pressure. Dilute the residue with EtOAc (90 mL) and H2O (50 mL). Separate the layers and wash the organic layer with brine (2×50 mL), dry over MgSO4; filter; and concentrate the filtrate under reduced pressure to provide a residue. Purify and separate isomers using chromatography conditions K (see below) collecting the second eluting isomer as the title compound (2.01 g, 13%). MS (m/z): 261 (M+18).

Provenance & Evidence