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, 30.70 mmol) was added to a mixture of N-benzyl-N-[2-benzyloxy-5-(2-bromoacetyl)phenyl]methanesulfonamide (131) (25.00 g, 51.20 mmol) and R-methyl-CBS-oxazoborolidine (1 M in toluene, 5.10 mL, 5.10 mmol) in anhydrous THF (150 mL). The reaction mixture was stirred at 0° C. for 15 min and then at rt for 16 h. Methanol (100 mL) was then slowly added to quench the reaction. After removal of solvent by rotary evaporation, the resulting residue was purified by column chromatography (silica gel, dichloromethane only) to give desired bromo alcohol 132 as an orange oil (23.80 g, 95% yield): 1H NMR (500 MHz, CDCl3) δ 2.86 (s, 3H), 3.30-3.38 (m, 2H), 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