Triethylamine → tert-butyl(3aR,4S,6aS)-2-(5-(trifluoromethyl)pyridin-2-yl)octahydrocyclopenta[c]pyrrol-4-ylcarbamate

Participants

Reaction Conditions

Reaction Steps

tert-Butyl(3aR,4S,6aS)-octahydrocyclopenta[c]pyrrol-4-ylcarbamate from Step B of Example 252 (250 mg, 1.105 mmol), 2-bromo-5-(trifluoromethyl)pyridine (250 mg, 1.105 mmol), and triethylamine (0.462 mL, 3.31 mmol) were combined in ethanol (0.6 mL). The reaction was heated at 81° C. for 16 hours. To the reaction mixture was added 50% water/ethanol (5 mL), and the precipitate was collected by filtration. This crude material was purified using a 12 g silica gel cartridge with a gradient of 0-1.5% methanol (2 N ammonia)/dichloromethane over 20 minutes to give tert-butyl(3aR,4S,6aS)-2-(5-(trifluoromethyl)pyridin-2-yl)octahydrocyclopenta[c]pyrrol-4-ylcarbamate: 1H NMR (500 MHz, pyridine-d5) δ ppm 8.62 (s, 1H), 7.76 (d, J=6.4, 1H), 7.68 (d, J=8.6, 1H), 6.38 (d, J=8.8, 1H), 4.10 (s, 1H), 3.73 (d, J=10.4, 1H), 3.65 (s, 1H), 3.61-3.53 (m, 1H), 3.32 (d, J=10.1, 1H), 2.82-2.71 (m, 2H), 2.15 (td, J=12.6, 6.8, 1H), 1.97 (dt, J=13.1, 6.4, 1H), 1.74 (dq, J=15.6, 7.9, 1H), 1.54 (s, 9H), 1.45-1.34 (m, 1H); MS (DCI+) m/z 372 (M+H)+.

Provenance & Evidence