1,3-Cyclohexadiene → HCID 11750599, compound

Participants

Reaction Steps

Dibenzyl 3-{(2S)-4-(2,5-difluorophenyl)-1-[(dimethylamino)carbonyl]-2,5-dihydro-1H-pyrrol-2-yl)phenyl phosphate (8-1, 108 mg, 0.18 mmol) was dissolved in 4:1 MeOH:cyclohexadiene (2 mL) and treated with 10% Palladium on carbon (100 mg). The reaction was stirred vigorously for 15 min, and then filtered over celite using MeOH to wash the compound throughly from the celite. The washings were concentrated and purified by reverse phase column chromatography (C-8, 10-90% CH3CN/H2O with 0.1% TFA gradient) to provide 3-{(2S)-4-(2,5-difluorophenyl)-1-[(dimethylamino)carbonyl]-2,5-dihydro-1H-pyrrol-2-yl}phenyl dihydrogen phosphate (8-2) as a white solid: 1H NMR (300 MHz, CD3OD) δ 7.20 (m. 7H), 6.42 (br s, 1H), 6.08 (m, 1H), 5.00 (dd, J=14.0, 3.6 Hz, 1H), 4.55 (d, J=14.0 Hz, 1H), 2.92 (s, 6H). LRMS m/z (M+H) 425.4 found, 425.3 required.

Provenance & Evidence