Sodium borohydride → HCID 66996649, compound

Participants

Reaction Conditions

Reaction Steps

(3aR,6aS)-2-Benzylhexahydrocyclopenta[c]pyrrol-4(5H)-one (1.462 g, 6.79 mmol) [prepared as described by Santora, V. J. et. al. Bioorganic & Medicinal Chemistry Letters (2008), 18, 1490-1494] was dissolved in methanol (20 mL) and cooled in a dry ice/acetone bath to −40° C. Sodium borohydride (0.514 g, 13.58 mmol) was added in portions over 5 minutes. The reaction mixture was 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 (3aR,4R,6aS)-2-benzyloctahydrocyclopenta[c]pyrrol-4-ol: 1H NMR (300 MHz, CDCl3) δ ppm 7.45-7.38 (m, 2H), 7.34 (dd, J=10.2, 4.7, 2H), 7.30-7.24 (m, 1H), 5.63 (s, 1H), 4.30 (dd, J=11.4, 6.2, 1H), 3.54 (q, J=13.0, 2H), 3.17 (dd, J=9.3, 3.3, 1H), 2.57 (dtd, J=10.0, 7.1, 3.2, 1H), 2.48 (dtt, J=17.5, 8.7, 4.3, 1H), 2.44-2.38 (m, 2H), 2.31 (dd, J=9.2, 7.4, 1H), 2.04-1.96 (m, 1H), 1.76-1.61 (m, 2H), 1.47-1.40 (m, 1H); MS (ESI+) m/z 217 (M+H)+.

Provenance & Evidence