Ethyl Acetate → HCID 86682411, compound

Participants

Reaction Steps

To a solution of 5-{[6-benzyloxy)pyridine-3-yl]methyl}-8-[(1S,2S)-2-hydroxycyclohexyl]-8,9-dihydro-7H-pyrrolo[3,4-h]quinolin-7-one (Example 19, 0.070 g, 0.15 mmol) in a mixture of 1 mL of ethyl acetate and 1 mL of ethanol under an atmosphere of nitrogen was added palladium on carbon (1.6 mg, 0.015 mmol). The mixture was placed under an atmosphere of hydrogen (1 atm) for 15 hr, filtered through a pad of Celite and concentrated in vacuo. The residue was purified via preparative reverse phase HPLC to provide the title compound that gave a proton NMR spectra consistent with theory and a mass ion (ES+) of 394.2134 for [M+H]+ [Calc'd for C23H28N3O3, [M+H]+=394.2134]: 1H NMR (400 MHz, CD3OD) δ 7.54-7.51 (m, 1H), 7.21 (d, J=1.8 Hz, 1H), 6.90 (s, 1H), 6.59 (d, J=9.4 Hz, 1H), 4.33-4.22 (m, 2H), 4.00-3.82 (m, 1H), 3.82 (s, 2H), 3.75-3.69 (m, 1H), 3.37-3.32 (m, 1H), 2.84-2.69 (m, 3H), 2.11-2.09 (m, 1H), 1.97-1.92 (m, 2H), 1.92-1.67 (m, 3H), 1.64-1.57 (m, 1H), 1.44-1.29 (m, 4H) ppm.

Provenance & Evidence