Methanol → (R)-1-(4-Benzyloxy-3-nitrophenyl)-2-bromoethanol

Participants

Reaction Steps

A solution of BH3.THF in THF (1 M, 3.70 mL, 3.70 mmol) was added to a solution of 1-(4-benzyloxy-3-nitrophenyl)-2-bromoethanone (3) (1.08 g, 3.08 mmol) and R-methyl-CBS-oxazoborolidine (1 M in toluene, 0.61 mL, 0.61 mmol) in anhydrous THF (15 mL). The resulting reaction mixture was stirred 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 dichloromethane to give the desired bromo alcohol 4 as a yellow, viscous oil (0.72 g, 66%): 1H NMR (500 MHz, CDCl3) δ 2.82 (d, 1H), 3.48 (dd, 1H), 3.59 (dd, 1H), 4.89 (m, 1H), 5.21 (s, 2H), (d, 1H), 7.39 (m, 5H), 7.50 (dd, 1H), 7.87 (d, 1H).

Provenance & Evidence