HCID 54674188, compound → HCID 54674340, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of N-{(3aR,4S,6aS)-4-methyl-2-[6-(trifluoromethyl)pyridin-2-yl]octahydrocyclopenta[c]pyrrol-4-yl}benzamide (180 mg, 0.462 mmol) from Example 15 in tetrahydrofuran (1 mL) was added dropwise borane tetrahydrofuran complex solution (1.387 mL, 1.387 mmol). The reaction was heated at 80° C. for 3 hours, quenched with 2 N HCl (0.5 mL) and then stirred for 1 hour. The reaction mixture was neutralized with aqueous sodium bicarbonate and extracted with dichloromethane. The combined organic washes were purified by silica gel chromatography using 1-10% methanol (2 N ammonia)/dichloromethane as eluent to give the title compound: 1H NMR (500 MHz, pyridine-d5) δ ppm 8.69 (d, J=8.0, 1H), 8.65 (d, J=7.4, 2H), 8.57-8.48 (m, 2H), 8.44 (t, J=7.3, 1H), 8.14 (d, J=7.2, 1H), 7.69 (d, J=8.6, 1H), 4.92-4.83 (m, 2H), 4.76-4.65 (m, 2H), 4.52-4.46 (m, 1H), 4.46-4.39 (m, 1H), 4.13-4.05 (m, 1H), 3.72 (dd, J=15.8, 7.9, 1H), 3.26 (dq, J=13.2, 8.3, 1H), 2.87-2.73 (m, 2H), 2.71-2.58 (m, 1H), 2.49 (dq, J=9.4, 5.0, 1H), 2.29 (s, 3H); MS (ESI+) m/z 376 (M+H)+.

Provenance & Evidence