Methyl iodide → 1-Benzyl 3-methyl pyrrolidine-1,3-dicarboxylate

Participants

Reaction Steps

To a solution of N-carbobenzyloxypyrrolidine-3-carboxylic acid (10.15 g, 40.72 mmol) and iodomethane (5.08 mL, 81.44 mmol) in N,N′-dimethylformamide (80 mL) was added powdered potassium hydrogen carbonate (8.15 g, 81.44 mmol) and the reaction mixture stirred at ambient temperature for 5 hours. The mixture was partitioned between ethyl acetate and brine and the organic phase washed with water and concentrated. The residue was purified by flash chromatography on silica gel using 5-50% ethyl acetate in hexane to give the title compound (10.59 g, 99%). MS(DCI): m/z 264 (M+H)+.

Provenance & Evidence