Cornforth reagent → HCID 59722632, compound

Participants

Reaction Steps

Pyridinium dichromate (7.92 g, 21.0 mmol) was added to a solution of crude tert-butyl {(3R,6S)-6-(2,3-difluorophenyl)-2-[(4,4,4-trifluoro-2-hydroxybutyl)imino]azepan-3-yl}carbamate (3.27 g, 7.01 mmol) in acetonitrile (70 mL). After 70 h, the mixture was filtered and concentrated. Saturated aqueous sodium bicarbonate was added and the mixture was extracted with dichloromethane (3×). The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated. Purification by silica gel chromatography (100% dichloromethane→96% dichloromethane/methanol) gave the title compound (2.35 g). MS 446.1 (M+1). 1H NMR (500 MHz, CDCl3) δ 7.14-7.09 (m, 1H), 6.97-6.94 (m, 2H), 6.33 (d, J=5.8 Hz, 1H), 4.82 (dd, J=10.0, 3.9 Hz, 1H), 4.12-4.07 (m, 1H), 3.99 (d, J=14.6 Hz, 1H), 3.37 (q, J=20.0, 10.0 Hz, 2H), 2.94 (t, J=110.2 Hz, 1H), 2.44 (d, J=13.7 Hz, 1H), 2.34-2.26 (m, 1H), 2.16-2.13 (m, 1H), 1.63-1.60 (m, 1H), 1.57 (s, 9H).

Provenance & Evidence