Sodium borohydride → (Meso-3aR,5r,6aS)-tert-butyl 5-hydroxyhexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate

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Reaction Steps

Compound 1019 (4 g; 0.018 mole) was dissolved in 50 mL of ethanol. Sodium borohydride was added at RT portionwise. After stirring for 3 hours, the reaction was concentrated in vacuo. The resulting oil was dissolved in DCM (200 mL), washed with water, brine, (Na2SO4), and concentrated in vacuo to yield (3aR,6aS)-tert-butyl 5-hydroxyhexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate as a yellow oil (Compound 1020, 3.79 g; 93% yield); 1H NMR (CDCl3): δ 4.2 (m, 1H), 3.55 (dd, 2H), 3.4 (dd, 2H), 2.7 (m, 2H), 2.2 (m, 2H), 1.6 (m, 2H), 1.5 (s, 9H).

Provenance & Evidence