2-Methoxypropene → HCID 57140265, compound

Participants

Reaction Steps

A solution of t-butyl (2R,3S)-3-tertbutoxycarbonylamino-2-hydroxy-3-phenylthiopropionate (0.060 g, 0.17 mmol) in toluene (8.0 ml) was treated with pyridinium p-toluene sulfonate (2.14 mg) and freshly distilled 2-methoxypropene (0.384 ml). The mixture was stirred at RT for 5 min, and at 80° C. for 4 h. After dilution with ethyl acetate (8 ml), the organic phase was washed with aqueous NaHCO3 sat. solution (3 ml), brine (2×3 ml), dried (Na2SO4), and evaporated to give a crude mixture. Purification via flash chromatography (hexanes-ethyl ether 95:5) gave pure t-butyl [(4S,5R)-N-tertbutoxycarbonyl-2,2-dimethyl-4-phenyl-1,3-oxazolidin-5-yl]thiocarboxylate (42.5 mg, 65.6%).

Provenance & Evidence