반응 #11227

반응 방정식

carbazole

6-Ally-4-(2-chlorophenyl)-2-(2,4-dimethoxybenzyl)-9-methoxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

N-methylmorpholine N-oxide

acetone water

→

diol

수율 94.0%

4-(2-Chlorophenyl)-6-(2,3-dihydroxypropyl)-2-(2,4-dimethoxybenzyl)-9-methoxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

수율 94.0%

용매

hydrochloric acid

ethyl acetate

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후처리

1. 1
   기타The organic phase was dried
2. 2
   기타the drying agent was removed
3. 3
   농축the solution was concentrated to dryness
4. 4
   기타Chromatography on silica eluting with ethyl acetatelhexane (2:1), followed by crystallization from diethyl ether/hexane

실험 절차

To a solution of carbazole (288) (80 mg, 0.14 mmol) procedure described in example 298 in acetone/water (4:1, 20 mL) was added N-methylmorpholine N-oxide (33 mg, 0.28 mmol) and osmium tetroxide (176 uL, 4% solution in water, ˜0.028 mmol). The reaction mixture was stirred at room temperature for 18 hours before being diluted with 1N hydrochloric acid and extraction with ethyl acetate. The organic phase was dried, the drying agent was removed and the solution was concentrated to dryness. Chromatography on silica eluting with ethyl acetatelhexane (2:1), followed by crystallization from diethyl ether/hexane gave diol (290) (80 mg, 94%) as a yellow powder, mp 151–156° C. 1H NMR δ [(CD3)2SO] 8.50 (d, J=2.6 Hz, 1H), 7.82 (s, 1H), 7.69 (br d, J=9.0 Hz, 1H), 7.58 (m, 1H), 7.52–7.46 (m, 3H), 7.30 (dd, J=9.0, 2.6 Hz, 1H), 6.95 (d, J=8.4 Hz, 1H), 6.57 (d, J=2.4 Hz, 1H), 6.44 (dd, J=8.4, 2.4 Hz, 1H), 5.02 (d, J=5.0 Hz, 1H), 4.87 (br s, 1H), 4.69 (s, 2H), 4.55 (m, 1H), 4.38 (m, 1H), 3.89 (m, 4H), 3.80 (s, 3H), 3.72 (s, 3H), 3.41 (partially obscured m, 2H). Found: C, 65.32; H, 5.00; N, 4.83. C33H29ClN2O7.1/4H2O requires: C, 65.45; H, 4.91; N, 4.63.

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