Diethyl Carbonate → HCID 66818424, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (S)-3-(4-bromo-3-methyl-phenylamino)-propane-1,2-diol (202 mg, 0.777 mmol), diethyl carbonate (3 ml), sodium methoxide (28% in MeOH, 0.160 ml) and MeOH (4 ml) was stirred at 130° C. overnight. The reaction mixture was treated with saturated NH4Cl and H2O and extracted with AcOEt (×2). The organic layers were combined and sequentially washed with H2O and saturated brine, and then dried over Na2SO4 and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane/AcOEt) to give (R)-3-(4-bromo-3-methyl-phenyl)-5-hydroxymethyl-oxazolidin-2-one (170 mg, 77%).

Provenance & Evidence