Methanol → N-Benzyl-N-[2-benzyloxy-5-(2-bromo-1-(R)-hydroxyethyl)phenyl]methane-sulfonamide

Participants

Reaction Conditions

Reaction Steps

A solution of BH3.THF in THF (1 M, 2.80 mL, 2.80 mmol) was added to a mixture of N-benzyl-N-[2-benzyloxy-5-(2-bromoacetyl)phenyl]methanesulfonamide (33) (1.09 g, 2.23 mmol) and R-methyl-CBS-oxazoborolidine (1 M in toluene, 0.45 mL, 0.45 mmol) in anhydrous THF (10 mL). The reaction mixture was stirred at 0° C. for 15 min and then at rt for 16 h. Methanol (5 mL) was slowly added to quench the reaction. After removal of solvent by rotary evaporation, the resulting residue was purified by Biotage silica gel column chromatography eluting with a mixture of ethyl acetate (0-3%) in dichloromethane to give the desired bromo alcohol 34 as a white solid (0.92 g, 84%): 1H NMR (500 MHz, CDCl3) δ 2.60 (s, 1H), 2.85 (s, 3H), 3.30 (m, 1H), 3.38 (m, 1H), 4.70 (m, 3H), 5.11 (s, 2H), 7.00 (m, 2H), 7.21 (m, 5H), 7.28 (d, 1H), 7.42 (m, 5H).

Provenance & Evidence