Ammonium Chloride → (S)-4-isopropyl-3-(3-phenylpropanoyl)oxazolidin-2-one

Participants

Reaction Conditions

Reaction Steps

Add n-butyllithium (2.5 M solution in hexanes, 32 mL of, 80 mmol) to a solution of 4-(S)-isopropyloxazolidin-2-one (10.26 g, 79.4 mmol) in THF (250 mL) at −78° C. Stir 30 min. Add 3-phenylpropionyl chloride (13.2 mL, 89 mmol) over 4 min. Stir 2.5 h at −78° C., then warm to −55° C. and stir 2 h. Add saturated aqueous ammonium chloride (75 mL) and warm to room temperature. Extract with dichloromethane and wash extract with 1 N NaOH (200 mL), saturated aqueous sodium chloride, dry (magnesium sulfate) and concentrate. Add hexanes (50 mL), filter solids and dry under vacuum to give a white solid (18.94 g, 91%).

Provenance & Evidence