Ethanol → (R)-2-amino-2-(5-bromo-2-fluorophenyl)propan-1-ol

Participants

Reaction Conditions

Reaction Steps

A solution of the (R)-4-(5-bromo-2-fluoro-phenyl)-4-methyl-oxazolidin-2-one (8.94 g, 33 mmol) in a 1:1-mixture of ethanol and water (120 ml) was treated with lithium hydroxide monohydrate (6.85 g, 163 mmol) and the reaction mixture was stirred at 100° C. overnight. For the workup, the reaction mixture was evaporated at reduced pressure and the residue dissolved in ethyl acetate (90 ml), then extracted with hydrochloric acid (2N, 90 ml). The aqueous layer was treated with a solution of sodium hydroxide (2N, 100 ml) and solid sodium chloride was added until saturation. The following extraction with ethyl acetate (3×200 ml) and the evaporation of the combined organic layers after drying over sodium sulphate yielded the (R)-2-amino-2-(5-bromo-2-fluoro-phenyl)-propan-1-ol as a white crystalline solid (7.90 g, 98% of theory, e.e.>98%).

Provenance & Evidence