(3RS,4SR)-1-Benzyl-4-(3,4-dichloro-phenyl)-pyrrolidine-3-carboxylic acid methoxy-methyl-amide → 1-[(3RS,4SR)-1-Benzyl-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-propan-1-one

Participants

Reaction Steps

To a solution of (3RS,4SR)-1-benzyl-4-(3,4-dichloro-phenyl)-pyrrolidine-3-carboxylic acid methoxy-methyl-amide (described herein above) 377 mg (0.959 mmol) dissolved in THF (4 mL) was added 0.676 mL (1.15 mmol) of ethyllithium (1.7M in dibutylether) dropwise at −78° C. and stirred for one hour. The reaction was quenched by aq. ammonium chloride solution and extracted with ethylacetate. The separated organic layer was dired on anhydrous sodium sulfate and concentrated in vaccuo. The residue was purified by silica gel column chromatography eluted by a mixture of heptane and ethyl acetate (10:1) yielding 212 mg (61%) of the title compound as a light yellow oil. ES-MS m/e: 362.2 (M+H+).

Provenance & Evidence