Hydrochloric Acid → ethyl (2RS,3RS)-3-(4-fluorophenyl)-3-hydroxy-2-((4-(trifluoromethyl)phenyl)methyl)propionate

To a solution of ethyl 3-(4-fluorophenyl)-3-oxo-2-((4-(trifluoromethyl)phenyl)methyl)propionate (6 g, 16.3 mmol) in methanol (100 ml) was added sodium borohydride (640 mg, 16.9 mmol) under ice-cooling, and the mixture was stirred for 20 min. The reaction solution was poured into 1N hydrochloric acid (50 ml), and extracted with ethyl acetate (100 ml×2). The extract was washed with water and saturated brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1) to give ethyl (2RS,3SR)-3-(4-fluorophenyl)-3-hydroxy-2-((4-(trifluoromethyl)phenyl)methyl)propionate (5.1 g, 84%) as a colorless oil.