Water → HCID 68576793, compound

Participants

Reaction Steps

To a stirred solution of 3-vinyl-N-(tert-butyloxycarbonyl)morphinan 44 (10.5 mg, 0.03 mmol) in acetone:water=2:1 solution (0.3 mL) were added N-methylmorpholine-N-oxide (10 μL, 50 wt. % in water), and osmium tetroxide (one drop) sequentially and the mixture was stirred for 2 h at rt. After starting material disappeared on TLC, ethyl acetate (2 mL) and aqueous Na2SO3 solution (2 mL) were poured into the mixture, and the organic layer was separated, dried over MgSO4, and concentrated. Column chromatography gave 10 mg (87%) of the title compound: 1H NMR (300 MHz, CDCl3) δ7.29˜7.36 (1H, m); 7.17˜7.10 (2H, m); 4.79 (1H, d); 4.37 (0.55H, br); 4.19 (0.45H, br); 3.77˜3.66 (3H, m); 3.11 (1H, m); 2.72˜2.41 (4H, m); 2.03 (1H, m); 1.71˜1.04 (19H, m).

Provenance & Evidence