Triacetoxyperiodinane → HCID 86718788, compound

Participants

Reaction Steps

The solution of the product of Example 40 (50 mg, 0.16 mmol) in dichloromethane (4 mL) at 0° C. was added sodium bicarbonate (13.4 mg, 0.16 mmol) and Dess-Martin periodinane (132 mg, 0.31 mmol). The reaction mixture was warmed to room temperature and stirred overnight. The reaction was quenched by the addition of 5% hydrochloric acid (5 mL) and then the organics were extracted with ethyl acetate (20 mL×3) and the organic phase was washed with saturated sodium bicarbonate (20 mL) and brine (20 mL), dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography to afford the title compound as a yellow solid (22.8 mg, Yield: 45%). Mp=35.2-38° C.; Rf=0.6 (10:1 petroleum ether/ethyl acetate); 1H NMR (400 MHz, CDCl3+D2O) δ 2.68 (d, J=11.2 Hz, 1H), 2.13-2.09 (m, 1H), 1.78 (dd, J=2.4 Hz 13.2 Hz, 1H), 1.55-1.50 (m, 2H), 1.39 (d, J=12.8 Hz, 1H), 1.31-1.24 (m, 1H), 1.06-0.98 (m, 1H), 0.94 (s, 3H), 0.89 (d, J=6.4 Hz, 3H), 0.86 (s, 3H) ppm; Mass spectrum (EI+ve) m/z 320 (M+); [α]D25=−88.0° (c=0.20, dichloromethane).

Provenance & Evidence