1,2-Dichloroethane → HCID 66936246, compound

Participants

Reaction Steps

A solution of commercially available phenylmethyl (trans)-3-[(dimethylamino)carbonyl]-4-methyl-1-pyrrolidinecarboxylate (1.06 g, 3.4 mmol), DMAP (0.63 g, 5.2 mmol), and EDC (1.0 g, 5.2 mmol) in DCM (18 mL) was stirred for 5 min and dimethylamine (1.9 mL, 3.8 mmol, 2M in THF) was added. The reaction was allowed to stir until it was judged to be complete by LCMS and was quenched with 1 M HCl. A standard work-up provided the desired amide intermediate. This material was immediately dissolved in degassed MeOH (20 mL) and 10% Pd/C (120 mg) was added. The reaction mixture was allowed to stir under a hydrogen balloon until complete deprotection was observed by LCMS. The catalyst was removed by filtration to yield (trans)-N,N,4-trimethyl-3-pyrrolidinecarboxamide. LCMS: (M+H)+: 157.2.

Provenance & Evidence