Triacetoxyperiodinane → HCID 86718788, compound

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).

1. customThe reaction was quenched by the addition of 5% hydrochloric acid (5 mL)
2. extractionthe organics were extracted with ethyl acetate (20 mL×3)
3. washthe organic phase was washed with saturated sodium bicarbonate (20 mL) and brine (20 mL)
4. dry with materialdried over anhydrous sodium sulfate
5. concentrationconcentrated under reduced pressure
6. customThe residue was purified by silica gel column chromatography

ORD record

ord-23e3f177ebea489488250ce4fe03c591

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09133082B2