Sodium borohydride → (3aS,4S,6aR)-2-benzyloctahydrocyclopenta[c]pyrrol-4-ol

Participants

Reaction Conditions

Reaction Steps

A mixture of (3aS,6aR)-2-benzylhexahydrocyclopenta[c]pyrrol-4(5H)-one (1.462 g, 6.79 mmol) from Step A in methanol (20 mL) was cooled in an dry ice/acetone bath to −40° C. Sodium borohydride (0.514 g, 13.58 mmol) was added in portions over 5 minutes. The reaction allowed to warm to room temperature overnight, then it was quenched with saturated aqueous ammonium chloride, diluted with water, and extracted with 3×150 mL of ethyl acetate. The combined extracts were dried (Na2SO4) and the solvent was removed in vacuo to give (3aS,4S,6aR)-2-benzyloctahydrocyclopenta[c]pyrrol-4-ol: 1H NMR (300 MHz, CDCl3) δ ppm 7.38-7.16 (m, 5H), 4.21-4.04 (m, 1H), 3.66 (d, J=12.8, 1H), 3.51 (d, J=12.8, 1H), 3.07 (d, J=9.3, 1H), 2.65-2.53 (m, J=11.8, 2H), 2.52-2.43 (m, 1H), 2.18-2.07 (m, J=7.5, 16.3, 2H), 2.05-1.94 (m, J=8.7, 12.6, 1H), 1.84-1.74 (m, J=6.2, 1H), 1.49-1.34 (m, 3H).

Provenance & Evidence