Acetic Acid → (2S,4R)-1-allyloxycarbonyl-4-methanesulfonyloxypyrrolidine-2-methanol

Participants

Reaction Steps

To a solution of lithium chloride (18.55 g, 437 mmol) and (2S,4R)-N-allyloxycarbonyl-4-methanesulfonyloxyproline methyl ester (67.2 g, 219 mmol) in tetrahydrofuran (280 ml) were successively added sodium borohydride (16.55 g, 437 mmol) and ethanol (420 ml) in one portion. The reaction mixture was stirred at room temperature for 5 hours, cooled to 5° C., treated carefully with acetic acid (25 ml, 437 mmol) to quench the reaction. The solvents were evaporated in vacuo, and the residue partitioned between ethyl acetate (300 ml) and water (300 ml). The organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, and evaporated to afford the title compound (56.26 g, 92% yield) as an oil.

Provenance & Evidence