Ethanol → 3-[((2R,3R)-1-methyl-5-oxo-3-phenylpyrrolidin-2-yl)carbonyl](4S)-4-benzyl-1,3-oxazolidin-2-one

Participants

Reaction Steps

To a slurry of 10% palladium on carbon (7.0 g) in EtOAc (700 mL) was added a solution of diastereomers 3-[((2R)-1-methyl-5-oxo-3-phenyl(3-pyrrolin-2-yl)carbonyl](4S)-4-benzyl-1,3-oxazolidin-2-one and (4S)-3-[((2S)-1-methyl-5-oxo-3-phenyl(3-pyrrolin-2-yl))carbonyl]-4-benzyl-1,3-oxazolidin-2-one (78.5 g, 0.208 mol) in EtOH (100 mL) and the reaction mixture was stirred under a H2 atmosphere (1 Atm) for 2 days. The reaction mixture was filtered through a pad of Celite® with the aid of EtOAc. The filtrate was concentrated under reduced pressure and purified by flash chromatography (gradient from 15% to 65% EtOAc/hex) to give diastereomer 3-[((2R,3R)-1-methyl-5-oxo-3-phenylpyrrolidin-2-yl)carbonyl](4S)-4-benzyl-1,3-oxazolidin-2-one as a single diastereomer (41.02 g, 52%): TLC (15% i-PrOH/hex) Rf0.25; 1H NMR (CDCl3) δ 1.39 (dd, J=11.4, 13.6 Hz, 1H), 2.45-2.51 (dd, J=3.3, 13.6 Hz, 1H), 2.87-2.91 (m, 5H), 3.91 (dd, J=9.2, 2.9 Hz, 1H), 4.03-4.23 (m, 3H), 4.36-4.43 (m, 1H), 5.75 (d, J=9.2 Hz, 1H), 7.01-7.03 (m, 2H), 7.21-7.39 (m, 8H); HPLC ES-MS m/z (rel abundance) 377 (MH+, 100%).

Provenance & Evidence