Water → HCID 86669801, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of 4-(4-chlorophenyl)-2-(morpholin-4-yl)-3-vinyl-5,6-dihydrothieno[2,3-c]pyridin-7(4H)-one (209.0 mg, 0.5575 mmol, single enantiomer of unknown configuration) in 1,4-dioxane (8.46 mL) and water (2.12 mL, 117 mmol) was cooled to 0° C. To the mixture was added sodium metaperiodate (0.477 g, 2.23 mmol), 2,6-lutidine (0.258 mL, 2.23 mmol), and a solution of 4% osmium tetroxide in water (68.1 uL, 0.0112 mmol). The reaction was vigorously stirred at 0° C. for 1 h. After 1 h, the ice-water bath was removed, and the reaction was stirred at rt for an hour. The reaction mixture was filtered through a celite pad, and the pad was washed with EtOAc. The filtrate was washed with 1N HCl (×2), brine, dried over Na2SO4, and concentrated in vacuo. The crude mixture was purified using column chromatography on silica gel (40 g ISCO column, continuous gradient 100% hexanes to 100% EA over 60 minutes) to give the title compound (176 mg orange oil, 84%). Final purification of 26 mg of this material by HPLC gave 16 mg pure product as a white solid. LCMS: (FA) ES+ 377, 379. 1H NMR (400 MHz, DMSO) δ 9.52 (s, 1H), 7.59 (d, J=4.5 Hz, 1H), 7.39-7.34 (m, 2H), 7.10-7.05 (m, 2H), 4.67 (d, J=4.4 Hz, 1H), 3.92 (dd, J=12.9, 5.1 Hz, 1H), 3.81-3.70 (m, 4H), 3.47-3.36 (m, 2H), 3.36-3.26 (m, 3H overlapping with H2O peak).

Provenance & Evidence