Hydrogen Peroxide → HCID 90408981, compound

Temperature

0 °C

To a solution of 4-(3-phenoxyphenyl)-1-vinyl-2-oxabicyclo[2.2.2]octane (14 mg, 0.046 mmol) in THF (1 mL) at 0° C. was added BH3.SMe2 complex (0.046 mL of a 2.0 M solution in Et2O; 0.091 mmol). The reaction mixture was stirred at 0° C. for 10 min and then warmed to rt. After stirring for 1 h at rt, the reaction mixture was cooled to 0° C. and a few drops of 1 N aqueous NaOH and 30% aqueous H2O2 solution were added. The resulting mixture was warmed to rt and stirred for 2 h. The reaction was diluted with EtOAc, washed with water and brine, dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by flash chromatography on SiO2 (0 to 70% gradient EtOAc:hexanes) to afford the title compound (9 mg, 57% yield) as a colorless oil. LCMS, [M+H]+=325.1. 1H NMR (400 MHz, CDCl3) δ 7.37-7.27 (m, 3H), 7.14-7.08 (m, 2H), 7.04-6.95 (m, 4H), 6.84 (ddd, J=8.1, 2.3, 0.8 Hz, 1H), 4.01-3.94 (m, 2H), 3.85-3.78 (m, 2H), 2.17-1.89 (m, 6H), 1.74-1.69 (m, 2H), 1.68-1.62 (m, 2H).

1. temperaturewarmed to rt
2. stirringAfter stirring for 1 h at rt
3. temperaturethe reaction mixture was cooled to 0° C.
4. temperatureThe resulting mixture was warmed to rt
5. stirringstirred for 2 h
6. washwashed with water and brine
7. dry with materialdried (MgSO4)
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customThe residue was purified by flash chromatography on SiO2 (0 to 70% gradient EtOAc:hexanes)

ORD record

ord-4834f535e95c46eb9381a65894796297

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08962660B2