(+/-)-(4R 5R*)-5-ethoxycarbonyl-1-methyl-4-(4-nitrophenyl)pyrrolidin-2-one → (+/-)-(4R*,5R)-5-ethoxycarbonyl-1-methyl-4-(4-aminophenyl)pyrrolidin-2-one

Participants

Reaction Steps

A solution of (±)-(4R*,5R*)-5-ethoxycarbonyl-1-methyl-4-(4-nitrophenyl)pyrrolidin-2-one (2.00 g, 6.85 mmol) in EtOAc (15 mL) was added to an argon flushed flask containing 10% palladium on carbon (160 mg). The resulting mixture was placed under an atmosphere of H2 and stirred for 18 h. The reaction mixture then was filtered through a pad of Celite®. The filtrate was concentrated under reduced pressure to give (±)-(4R*,5R*)-5-ethoxycarbonyl-1-methyl-4-(4-aminophenyl)pyrrolidin-2-one (1.66 g, 92%) as a pale oil: TLC (EtOAc) Rf0.48; HPLC ES-MS m/z (rel abundance) 263 (MH+, 100%).

Provenance & Evidence