Tetrahydrofuran → HCID 66591138, compound

Participants

Reaction Conditions

Reaction Steps

N-((3aS,4S,6aR)-2-Benzyloctahydrocyclopenta[c]pyrrol-4-yl)-3-(trifluoromethyl)benzenesulfonamide (0.4237 g, 0.998 mmol) from Step A in tetrahydrofuran (10 mL) was added to 20% palladium hydroxide on carbon (wet, 0.085 g, 0.603 mmol) in a 50 mL pressure bottle under nitrogen. The reaction mixture was then placed under a hydrogen atmosphere (30 psi) and shaken at 50° C. for 18 hours. The mixture was filtered through a nylon membrane and the solvent was removed in vacuo. The crude material was purified by silica gel chromatography using 1-10% methanol (2 N ammonia)/dichloromethane supplied the title compound: 1H NMR (500 MHz, pyridine-d5) δ ppm 8.50 (s, 1H), 8.38 (d, J=7.9, 1H), 7.85 (d, J=7.8, 1H), 7.68 (t, J=7.8, 1H), 3.89 (dd, J=8.4, 14.2, 1H), 3.82 (t, J=6.2, 2H), 2.82 (dd, J=3.3, 9.7, 1H), 2.62 (qd, J=3.4, 7.9, 1H), 2.42-2.36 (m, 1H), 2.32 (d, J=4.5, 2H), 2.26 (dd, J=6.8, 11.7, 2H), 2.10 (t, J=8.7, 1H), 1.91-1.82 (m, 1H), 1.74-1.67 (m, 2H), 1.64-1.49 (m, 5H), 1.32 (dd, J=6.1, 9.6, 1H); MS (ESI+) m/z 407 (M+H)+.

Provenance & Evidence