Ethyl 1-methyl-5-oxo-3-phenyl-3-pyrroline-2-carboxylate → (+/-)-(4R*,5R*)-5-(ethoxycarbonyl)-1-methyl-4-phenylpyrrolidin-2-one

Participants

Reaction Steps

A mixture of ethyl 1-methyl-5-oxo-3-phenyl-3-pyrroline-2-carboxylate (1 g, 4 mmol) and 10% palladium on carbon (0.1 g) in EtOH (30 mL) was stirred under a H2 atmosphere (1 Atm) for 1 hour. The reaction mixture was filtered through a pad of Celite® with the aid of CH2Cl2. The filtrate was concentrated under reduced pressure to yield (±)-(4R*,5R*)-5-(ethoxycarbonyl)-1-methyl-4-phenylpyrrolidin-2-one (1 g, 100%): TLC (40% EtOAc/hex) Rf 0.13; 1H NMR (CDCl3) δ 0.83 (t, J=7.4 Hz, 3H), 2.64-2.72 (dd, J=8.8, 16.5 Hz, 1H), 2.88-3.0 (m, 4H), 3.65-4.0 (m, 4H), 4.34-4.36 (d, J=8.9 Hz, 1H), 7.2-7.35 (m, 5H), HPLC ES-MS m/z (rel abundance) 248 (MH+, 100%).

Provenance & Evidence