Acetic Acid → HCID 69853737, compound

Participants

Reaction Steps

A solution of 4-benzyl-5-(3-ethoxycarbonyl-2-oxo-propyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (10 g) in ethanol (100 ml) was stirred at 15° C. under an atmosphere of nitrogen during the portion-wise addition of sodium borohydride (450 mg). The solution was stirred for a further 30 minutes, treated with glacial acetic acid (2 ml) and evaporated. The residue was partitioned between diethyl ether (200 ml) and 2M aqueous hydrochloric acid (100 ml). The organic solution was washed sequentially with water, 5% aqueous sodium bicarbonate solution, water and saturated aqueous sodium chloride solution, dried (anhydrous magnesium sulfate) and evaporated to give 4-benzyl-5-(3-ethoxycarbonyl-2-hydroxy-propyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (10.11 g, 100%). Mass spectrum 422 [M+H]+.

Provenance & Evidence