1-benzyl hydrogen (R)-pyrrolidine-1,2-dicarboxylate → (R)-Benzyl 2-(2-carbamoyl-1H-pyrrol-1-ylcarbamoyl)pyrrolidine-1-carboxylate

Participants

Reaction Steps

A mixture of 1-amino-1H-pyrrole-2-carboxamide (6.00 g, 48.0 mmol) and (R)-1-(benzyloxycarbonyl)pyrrolidine-2-carboxylic acid (14.3 g, 57.5 mmol) was dissolved in THF (480 mL). To this solution was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (11.0 g, 57.5 mmol). The reaction was stirred overnight at rt then concentrated in vacuo. The residue was dissolved in CH2Cl2 (400 mL), washed with water (3×400 mL) and brine (400 mL), then dried (MgSO4), filtered, and concentrated in vacuo to give slightly impure 11A (17.65 g, >100%). 11A had an analytical HPLC retention time=2.103 min (Phenomenex Luna 3.0×50 mm, 10-90% aqueous MeOH over 5 min containing 0.1% TFA) and a LC/MS M++1=357.

Provenance & Evidence