Lithium diisopropylamide → 3-(4-Bromo-2-chloro-benzyl)-1-cyclohex-3-enyl-pyrrolidin-2-one

Participants

Reaction Conditions

Reaction Steps

Dissolve 1-cyclohex-3-enyl-pyrrolidin-2-one (Preparation 66) (300 mg, 1.82 mmol) in anhydrous THF (8 mL), cool to −78° C. and add LDA (2M in THF, 1.36 mL, 2.72 mmol) dropwise. After 10 minutes add 4-bromo-1-bromomethyl-2-chloro-benzene (512 mg, 1.82 mmol) and allow the mixture to warm to room temperature over 16 h. Quench with saturated aqueous ammonium chloride, extract with dichloromethane, dry the organic layer over sodium sulfate and evaporate. Purify the residue by chromatography on silica gel (eluting 0 to 50% ethyl acetate in hexane) to give the title compound as a clear oil (370 mg, 56%): MS (EI) m/z=367,369 (M+).

Provenance & Evidence