(4R,5S)-(+)-4-Methyl-5-phenyl-2-oxazolidinone → (4R,5S)-3-[3-(4-Chlorophenyl)-propionyl]-4-methyl-5-phenyl-oxazolidin-2-one

Participants

Reaction Conditions

Reaction Steps

nBuLi (1.6M in hexanes, 20 mL, 32 mmol) was added to a stirred solution of (4R,5S)-4-Methyl-5-phenyl-oxazolidin-2-one (5.2 g, 29 mmol) in THF (60 mL) at −78 C under N2. The solution was stirred at −78° C. for 10 mL and then 3-(4-Chlorophenyl)-propionyl chloride (6.0 g, 29 mmol) was added and the solution allowed to warm to room temperature over 1 hour. The solution was quenched with saturated aqueous NH4Cl, extracted into DCM (2×200 mL), dried over Na2SO4 and concentrated in vacuo. The product was purified by column chromatography on silica (50% EtOAc/hexanes) to give (4R,5S)-3-[3-(4-Chlorophenyl)-propionyl]-4-methyl-5-phenyl-oxazolidin-2-one (4.8 g, 48%.) 1H NMR (CDCl3, 400 MHz) δ 7.44-7.35 (3H, m), 7.30-7.24 (4H, m), 7.19 (2H, d, J 8.0 Hz), 5.64 (1H, d, J 7.4 Hz), 4.77-4.71 (1H, m), 3.34-3.17 (2H, m), 2.98 (2H, t, J 7.7 Hz), 0.88 (3H, d, J 6.7 Hz.)

Provenance & Evidence