Sodium Chloride → (S)-4-BENZYL-3-(3-PHENYLPROPANOYL)OXAZOLIDIN-2-ONE

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Reaction Steps

48.1 ml (77 mmole) of butyllithium (as a 1.6M solution in hexane) were added dropwise, at -78° C. and under an atmosphere of nitrogen, to a solution of 12.41 g (70 mmole) of (4S)-(-)-4-benzyl-2-oxazolidinone in 200 ml of anhydrous tetrahydrofuran, and the mixture was stirred for 30 minutes. At the end of this time, a solution of 13.0 g (77 mmole) of 3-phenylpropionyl chloride in 100 ml of anhydrous tetrahydrofuran was slowly added dropwise to the mixture, and the mixture was stirred for 1 hour. The mixture was then mixed with a saturated aqueous solution of sodium chloride and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated by distillation under reduced-pressure. The residue was purified by column chromatography through silica gel (using a 1:4 by volume mixture of ethyl acetate and hexane as the eluent) to afford 16.8 g (yield 78%) of the title compound as white crystals, melting at 92°-95° C.

Provenance & Evidence