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

HRID 11131

반응식

HRID 11131 반응식
C(N1C2C=[C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[Cl:23])[C:13]3[C:24](=[O:39])[N:25]([CH2:28][C:29]4[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][C:30]=4[O:37][CH3:38])[C:26](=O)[C:12]=3[C:11]=2[C:10]2[CH:9]=[C:8]([O:40][CH3:41])[CH:7]=[CH:6]C1=2)C=C.[CH3:42][N+:43]1([O-])[CH2:48][CH2:47][O:46][CH2:45][CH2:44]1.C[C:51](C)=[O:52].[OH2:54]>Cl.C(OCC)(=O)C.[Os](=O)(=O)(=O)=O>[Cl:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[C:14]1[C:13]2[C:24](=[O:39])[N:25]([CH2:28][C:29]3[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][C:30]=3[O:37][CH3:38])[C:26](=[O:54])[C:12]=2[C:11]2[C:10]3[CH:9]=[C:8]([O:40][CH3:41])[CH:7]=[CH:6][C:42]=3[N:43]([CH2:48][CH:47]([OH:46])[CH2:51][OH:52])[C:44]=2[CH:45]=1

참가 물질

7

반응물 3

HCID 82029Methyl morpholine oxideHCID 18366337Propan-2-one--water (1/1)HCID 695854926-Ally-4-(2-chlorophenyl)-2-(2,4-dimethoxybenzyl)-9-methoxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

생성물 1

HCID 219808174-(2-Chlorophenyl)-6-(2,3-dihydroxypropyl)-2-(2,4-dimethoxybenzyl)-9-methoxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione수율 94%

시약·촉매·용매 3

HCID 30318Osmium Tetroxide촉매HCID 313Hydrochloric Acid용매HCID 8857Ethyl Acetate용매

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.

후처리

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

출처 및 근거

ORD 기록
ord-f5196dcb4161474bbb05e2f36ea37b3b
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07094798B1

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