Hydrochloric Acid → HCID 66996984, compound

Participants

Reaction Steps

tert-Butyl(3aR,4S,6aS)-2-(3-(trifluoromethyl)phenyl)octahydrocyclopenta[c]pyrrol-4-ylcarbamate (29 mg, 0.078 mmol) from Step A was treated with 4 N hydrogen chloride in 1,4-dioxane (0.5 mL, 2 mmol) for 3 hours at room temperature. The solvent was removed under a stream of nitrogen and the residue basified with aqueous sodium bicarbonate and extracted with 2×2 mL of dichloromethane. The extracts were applied directly to a 12 g silica gel cartridge and purified with a gradient of 1-10% methanol in (2 N ammonia)/dichloromethane to give the title compound: 1H NMR (400 MHz, pyridine-d5) δ ppm 7.35 (t, J=7.9, 1H), 7.06 (d, J=7.6, 1H), 6.91 (s, 1H), 6.77 (dd, J=8.3, 2.4, 1H), 3.23-3.14 (m, 3H), 3.11 (dd, J=12.0, 5.7, 1H), 2.95 (dd, J=9.7, 4.4, 1H), 2.80-2.70 (m, 1H), 2.37-2.29 (m, 1H), 2.05 (ddt, J=16.5, 12.9, 6.3, 1H), 1.94-1.84 (m, 1H), 1.82-1.60 (m, 2H), 1.47-1.29 (m, 2H); MS (ESI+) m/z 271 (M+H)+.

Provenance & Evidence