4-Toluenesulfonyl chloride → HCID 67499866, compound

Participants

Reaction Conditions

Reaction Steps

Stir 4-(3-fluoro-phenyl)-N-(4-trifluoromethoxy-phenyl)-4-hydroxy-butyramide (2.45 g, 6.86 mmol) and p-toluenesulfonyl chloride (1.63 g, 8.60 mmol) in dry tetrahydrofuran (30 mL) under nitrogen. Cool to −40° C. and slowly add potassium t-butoxide (1M in tetrahydrofuran) (17.2 mL, 17.2 mmol). Allow to warm slowly to room temperature and stir for 2 hours. Add aqueous NH4Cl solution and extract with ethyl acetate, wash with brine and dry over anhydrous magnesium sulfate. Evaporate and purify on a silica gel column (dichloromethane-ethyl acetate) to give (±)-5-(3-fluoro-phenyl)-1-(4-trifluoromethoxy-phenyl)-pyrrolidin-2-one (1.9 g, 82% yield) MS (m/z): 340 (M+1). Instrumentation

Provenance & Evidence