Dimethylamine → Ethyl 4-[(dimethylamino)methyl]-1H-pyrrole-2-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a mixture of ethyl 4-formylpyrrole-2-carboxylate (8.8 g, 52.7 mmol) and dimethylamine (2 M in THF, 40 mL, 1.5 equiv) in methanol (60 mL) was added sodium cyanoborohydride (3.3 g, 1 equiv) in portions and the mixture was stirred for 3 h at 20° C. Water was added and the mixture was extracted with EtOAc. The combined organic layer was washed with water and dried over Na2SO4. Evaporation of solvent afforded a crude, which was purified by column chromatography on silica gel, eluted with MeOH-DCM (1:9) to afford ethyl 4-dimethylaminomethyl-pyrrole-2-carboxylate as a solid (7.8 g, 76%). MS (ES): 392 (MH+) 197.

Provenance & Evidence