1,2-Dichloroethane → 1-Tert-butyloxycarbonyl-cis-2-{[methoxy(methyl)amino]carbonyl}-5-phenylpyrrolidine

Participants

Reaction Steps

A solution of racemic N-Boc-cis-5-phenylproline (2 g, 6.865 mmol) in DMF (35 mL) was added HOBt (1.05 g, 6.87 mmol), EDC (1.97 g, 10.3 mmol), O, N-dimethylhydroxylamine hydrochloride (1.00 g, 10.3 mmol) and DIEA dropwise (1.33 mL, 10.3 mmol). The reaction was stirred at ambient temperature for 30 min and then partitioned between ethyl acetate and water. The EtOAc layer was separated and washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was subjected to column chromatography on silica gel eluting with 50:50 ethyl acetate and hexane. Collection and concentration of appropriate fractions provided the title compound. HPLC RT=3.46 min, 86% at 215 nm (Method A); ES MS (M+H)=335.3.

Provenance & Evidence