(1R,3S)-3-[(2-methylpropan-2-yl)oxycarbonylamino]cyclopentane-1-carboxylic acid → tert-butyl N-((1R,3S)-3-(hydroxymethyl)cyclopentyl)carbamate

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Reaction Steps

(1R,3S)-3-t-Butoxycarbonylaminocyclopentanecarboxylic acid (229 mg, 1 mmol) was dissolved in THF (10 mL) and borane-THF (1.5 mL, 1M solution) was added drop-wise at 0° C. and stirred overnight at r.t. The reaction mixture was poured into ice-cold water (10 mL) and extracted with ethyl acetate (2×50 mL). The ethyl acetate extract was washed with brine, dried over sodium sulfate, filtered and evaporated to yield a semi solid (160 mg, 74%). ESMS (+): 216 (M+1)+, 250 (M+Cl)+.

Provenance & Evidence