Hexane → (4R)-(1-methylethyl)-3-(3(R)-methyl-1-oxo-3-phenylpropyl)-2-oxazolidinone

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Reaction Steps

In a separate preparation, a solution of 4(R)-(1-methylethyl)-2-oxazolidinone (3.06 g, 23.7 mmol) in dry THF (30 mL) was cooled to -50°. Under argon, a 1.6M hexane solution of butyllithium (14.8 mL, 23.7 mmol) was added dropwise to the cooled solution of the oxazolidinone derivative. After 15 min at -78°, a solution of the first reactant in dry THF (10 mL) was added. The reaction mixture was stirred at -70° for 30 minutes and then allowed to warm to room temperature over a 45 min period. The mixture was quenched with excess 10% aqueous NH4Cl. Thereafter, the THF was removed under reduced pressure and the resulting concentrate was dissolved in EtOAc. The solution was washed with 5% aqueous NaHCO3 (2 X) and brine (2 X), dried (MgSO4) and concentrated to give an oil. The oil was purified by flash chromatography [SiO 2, hexane-EtOAc (43:7)] to yield (4R)-(1-methylethyl)-3-(3(R)-methyl-1-oxo-3-phenylpropyl)- 2-oxazolidinone (6.1 g, 93% yield).

Provenance & Evidence