Ammonium Chloride → (2S,4R)-Tert-butyl 2-(hydroxymethyl)-4-(methylsulfonyloxy)pyrrolidine-1-carboxylate

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Reaction Steps

Lithium borohydride (3.6 g, 163.0 mM) was added to a solution of methyl (2S,4R)-N-tert-butoxycarbonyl-4-methanesulfonyloxypyrrolidine-2-carboxylate (26.5 g, 81.5 mM) in anhydrous tetrahydrofuran (300 ml) with ice-cooling in a nitrogen gas stream and the mixture was stirred at room temperature for 3 hours. The reaction mixture was ice-cooled again, the reaction was ceased by adding dropwise a saturated aqueous solution of ammonium chloride carefully and the solvent was removed. The residue was poured into water, the insoluble matters were dissolved using 1N hydrochloric acid, the mixture was extracted with ethyl acetate and the organic layer was washed with 1N hydrochloric acid, water, a saturated aqueous solution of sodium bicarbonate, water and brine in this order and dried over anhydrous magnesium sulfate. The solvent was removed to give the title compound almost quantitatively (24 g).

Provenance & Evidence