Pyridine, hydrofluoride (1:1) → HCID 71043121, compound

Participants

Reaction Steps

To a solution of 1-({2-[(1S,2S)-2-{[tert-butyl(dimethyl)silyl]oxy}cyclohexyl]-1-methyl-3-oxo-2,3-dihydro-1H-benzo[e]isoindol-5-yl}methyl)-4-(pyridin-2-yl)piperidine-4-carbonitrile (0.120 g, 0.197 mmol) in 0.1 mL of pyridine was added hydrogen fluoride pyridine (0.098 g, 0.98 mmol). After 15 hr, the mixture was treated with saturated aqueous sodium bicarbonate and extracted 2× with ethyl acetate. The combined organic extracts were washed with brine, dried with magnesium sulfate, filtered, and concentrated in vacuo. The residue was purified via silica gel chromatography, eluting with 10-100% ethyl acetate in hexanes, to provide the titled compound that gave a proton NMR spectra consistent with theory and a mass ion (ES+) of 495.2765 for [M+H]+ [calc'd for C31H35N4O2, [M+H]+=495.2755]: 1H NMR (400 MHz, CDCl3) δ 8.60-8.58 (m, 1H), 8.45-8.41 (m, 1H), 7.95-7.90 (m, 1H), 7.83-7.79 (m, 1H), 7.74-7.69 (m, 1H), 7.66-7.56 (m, 3H), 7.25-7.21 (m, 1H), 5.11-5.03 (m, 2H), 4.42 (br s, 1H), 4.03-3.98 (m, 2H), 3.79-3.72 (m, 1H), 3.65-3.59 (m, 1H), 3.06-3.02 (m, 2H), 2.88-2.86 (m, 1H), 2.67-2.59 (m, 2H), 2.35-2.17 (m, 2H), 2.09-2.06 (m, 1H), 2.04-1.81 (m, 2H), 1.42-1.22 (m, 4H), 0.96-0.83 (m, 4H) ppm.

Provenance & Evidence