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

Participants

Reaction Conditions

Reaction Steps

To a solution of (2S,4R)-1-allyloxycarbonyl-2-methoxycarbonyl-4-methanesulfonyloxypyrrolidine (281 g) in a mixture of ethanol (0.9 l) and tetrahydrofuran (0.6 l) was added sodium borohydride (69.2 g) at 5° C. and the resulting mixture was allowed to stir for 3.5 hours at 20°-27° C. After cooling to -60° C., the reaction mixture was taken up into a mixture of 12N hydrochloric acid (152.4 ml), water (2.5 l) and ethyl acetate (2.5 l) at 0° C. The organic layer was separated and the aqueous layer was extracted with ethyl acetate (2 l). The organic layer and the extract were combined, washed with 2 portions of brine (500 ml×2), dried over magnesium sulfate and evaporated to give (2S,4R)-1-allyloxycarbonyl-2-hydroxymethyl-4-methanesulfonyloxypyrrolidine (226.9 g).

Provenance & Evidence