Methyl iodide → (S)-3-((R)-2-(4-methoxyphenyl)propanoyl)-4-benzyloxazolidin-2-one

Participants

Reaction Conditions

Reaction Steps

A solution of (S)-4-benzyl-3-(2-(4-methoxyphenyl)acetyl)oxazolidin-2-one (1.00 g, 3.07 mmol) in dry THF (10 ml) was added to lithium diisopropyl amide (400 mg, 3.69 mmol, 0.1 M) at −78° C. The reaction mixture was stirred for 2 h. Iodomethane (2.00 g, 14.1 mmol) was added to the reaction mixture and warmed to −20° C. and stirred for another 2 h. The reaction mixture was quenched with saturated ammonium chloride solution (20 ml) and extracted with ethyl acetate (3×25 ml). The combined organic layers was dried over anhydrous sodium sulfate, filtered and concentrated. The crude compound was purified by column chromatography over silica gel (60-120 mesh) using ethyl acetate (10%) in petroleum ether as eluent to afford 350 mg (33.8%) of (S)-3-((R)-2-(4-methoxyphenyl)propanoyl)-4-benzyloxazolidin-2-one as light yellow solid.

Provenance & Evidence