Sodium borohydride → (1R,2S,3R,5R)-3-[(tert-Butoxycarbonyl)amino]5-(hydroxymethyl)cyclopentane-1,2-diyl dibenzoate

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Reaction Steps

To a solution of tert-butyl (1R,4S,5R,6S)-5,6-bis(benzoyloxy)-3-oxo-2-azabicyclo[2.2.1]heptane-2-carboxylate (2.09 g, 4.62 mmol) in MeOH (60.0 mL) was added sodium borohydride (700. mg, 18.5 mmol) at 0° C. and the reaction was allowed to warm to rt. After 1.5 h, the mixture was quenched with 1.00 N HCl solution (20.0 mL), and concentrated in vacuo. The aqueous layer was extracted with DCM (3×50 mL) and the combined organic layers were washed with H2O (100. mL), dried over MgSO4 and concentrated in vacuo. The residue was purified via silica gel chromatography eluting with a gradient of 20 to 60% EtOAc in hexanes to afford the title compound (1.50 g, 80%). LC/MS: Rt=1.95 min, ES+ 456 (FA standard).

Provenance & Evidence