Aluminium lithium hydride → HCID 66590165, compound

Participants

Reaction Conditions

Reaction Steps

tert-Butyl(3aR,4S,6aS)-2-(2-chloro-4-(trifluoromethyl)phenylsulfonyl)octahydrocyclopenta[c]pyrrol-4-ylcarbamate (62 mg, 0.132 mmol) from Example 284 Step A was dissolved in 1,2-dimethoxyethane (1.0 mL) and lithium aluminum hydride (10.04 mg, 0.264 mmol) was added portionwise. The reaction was stirred at 70° C. overnight, then it was quenched with wet sodium sulfate. The crude material was applied to a 4 g silica gel cartridge and purified with a gradient of 1-10% methanol (2 N ammonia)/dichloromethane over 20 minutes to give (3aR,4S,6aS)-2-(2-chloro-4-(trifluoromethyl)phenylsulfonyl)-N-methyloctahydrocyclopenta[c]pyrrol-4-amine: 1H NMR (500 MHz, pyridine-d5) δ ppm 8.46 (s, 1H), 8.34 (d, J=8.2, 1H), 7.99 (s, 1H), 4.92 (s, 3H), 4.32 (dt, J=13.7, 7.0, 1H), 3.89 (dd, J=10.2, 3.0, 1H), 3.49 (dd, J=10.2, 7.5, 1H), 3.41-3.30 (m, 2H), 2.70-2.59 (m, 2H), 2.48 (dt, J=4.4, 2.2, 1H), 2.01 (td, J=11.8, 6.6, 1H), 1.95-1.83 (m, 1H), 1.59 (ddd, J=16.1, 10.8, 7.7, 1H), 1.37 (dt, J=22.2, 6.5, 1H); MS (APCI+) m/z 383 (M+H)+.

Provenance & Evidence