Carbon Tetrachloride → HCID 59656620, compound

Participants

Reaction Conditions

Reaction Steps

(2S)-4-(2,5-difluorophenyl)-2-(3-hydroxyphenyl)-N,N-dimethyl-2,5-dihydro-1H-pyrrole-1-carboxamide (4-2, 97 mg, 0.28 mmol) in anhydrous CH3CN (1.0 mL) at 0° C. was treated sequentially with iPr2NEt (0.10 mL, 0.6 mmol), CCl4 (0.14 mL, 1.5 mmol), DMAP (catalytic) and lastly dibenzyl phosphite (0.09 mL, 0.40 mmol) and the resulting off-yellow solution was stirred 2 h at 25° C. Upon completion, the reaction was concentrated and directly subjected to flash column chromatography (SiO2, 0-100% EtOAc/hexanes gradient) to provide dibenzyl 3-{(2S)-4-(2,5-difluorophenyl)-1-[(dimethylamino)carbonyl]-2,5-dihydro-1H-pyrrol-2-yl}phenyl phosphate (8-1) as a clear oil: 1H NMR (300 MHz, CDCl3) δ 7.30 (m, 11H), 7.15 (m, 2H), 7.05 (m, 2H), 6.96 (m, 2H), 6.32 (br s, 1H), 6.10 (m, 1H), 5.12 (d, J=1.8 Hz, 2H), 5.09 (d, J=1.8 Hz, 2H), 4.78 (ddd, J=13.7, 5.8, 1.8 Hz, 1H), 4.47 (d, J=13.7 Hz, 1H), 2.85 (s, 6H). LRMS m/z (M+H) 605.6 found, 605.6 required.

Provenance & Evidence