반응 #726697

반응 방정식

3-vinyl-N-(tert-butyloxycarbonyl)morphinan

water

N-methylmorpholine-N-oxide

Na2SO3

→

title compound

수율 87.0%

3-(1′,2′-dihydroxyethyl)-N-(tert-butyloxycarbonyl)morphinan

수율 87.0%

용매

ethyl acetate

acetone

반응 조건

후처리

1. 1
   workup.ADDITIONwere poured into the mixture
2. 2
   기타the organic layer was separated
3. 3
   건조dried over MgSO4
4. 4
   농축concentrated

실험 절차

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).

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