Bromoacetonitrile → 1-Cyanomethyl-5-oxo-pyrrolidine-2-carboxylic acid methyl ester

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Reaction Steps

To a solution of 5-oxo-pyrrolidine-2-carboxylic acid methyl ester (3 g, 21 mmol) in CH3CN (60 ml), 60% NaH (863 mg, 22 mmol) was added at 0° C. After stirring for 30 minutes, a solution of 2-bromoacetonitrile (2.59 g, 21 mmol) in CH3CN (10 ml) was added dropwise. After warming at room temperature, and stirring for 20 hours, the solvent was evaporated under reduced pressure. The residue was partitioned between water and ethyl acetate, the organic layer was washed with brine, dried (Na2SO4) and evaporated. The residue was purified by flash chromatography (from DCM to DCM/MeOH 95/5 respectively) to afford the title compound as a pale yellow oil (1.1 g, 29% yield).

Provenance & Evidence