HCID 66606939, compound → HCID 46834379, compound

Participants

Reaction Steps

A solution of 5-cyclohexenyl-N2-(tetrahydro-2H-pyran-4-yl)-2,3,4,9-tetrahydro-1H-carbazole-2,8-dicarboxamide (Example 3-117, 28 mg, 0.066 mmol) in methanol (10 mL) was combined with 10% palladium on charcoal (80 mg) and shaken under an atmosphere of hydrogen (45 psi) for 1 h. The mixture was filtered, the solid was rinsed with methanol and the filtrates were concentrated to provide 5-cyclohexyl-N2-(tetrahydro-2H-pyran-4-yl)-2,3,4,9-tetrahydro-1H-carbazole-2,8-dicarboxamide as an off-white solid (28 mg, quantitative). 1H NMR (400 MHz, methanol-d4) δ 7.46-7.50 (1H, m), 6.91 (1H, d, J=8.05 Hz), 3.89-3.98 (3H, m), 3.46-3.54 (2H, m), 3.13 (1H, dd, J=14.43, 4.16 Hz), 2.95-3.06 (2H, m), 2.87-2.94 (1H, m), 2.65-2.73 (1H, m), 2.15 (1H, dd, J=11.10, 3.05 Hz), 1.77-1.99 (8H, m), 1.47-1.61 (6H, m), 1.26-1.40 (2H, m). Mass spectrum m/z 424.3 (M+H)+.

Provenance & Evidence