Ethanol → 5-Benzyloxy-2-(4-benzyloxyphenyl)-3-((but-3-enyloxy)methyl)-1-ethylpyrrolo[2,1,5-cd]indolizine

HRID 1422086노트

반응식

HRID 1422086 반응식
N1CCCCC1.[H-].[Na+].[CH2:9]([O:16][C:17]1[C:18]2[N:19]3[C:23](=[CH:24][CH:25]=1)[C:22]([CH2:26][CH3:27])=[C:21]([C:28]1[CH:33]=[CH:32][C:31]([O:34][CH2:35][C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)=[CH:30][CH:29]=1)[C:20]3=[C:42]([CH2:44][O:45][CH2:46][CH2:47][CH2:48][CH2:49]Cl)[CH:43]=2)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(O)C>CN(C)C=O.O>[CH2:9]([O:16][C:17]1[C:18]2[N:19]3[C:23](=[CH:24][CH:25]=1)[C:22]([CH2:26][CH3:27])=[C:21]([C:28]1[CH:33]=[CH:32][C:31]([O:34][CH2:35][C:36]4[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=4)=[CH:30][CH:29]=1)[C:20]3=[C:42]([CH2:44][O:45][CH2:46][CH2:47][CH:48]=[CH2:49])[CH:43]=2)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

참가 물질

7

반응물 4

HCID 702EthanolHCID 8082PiperidineHCID 24758Sodium hydrideHCID 187069385-Benzyloxy-2-(4-benzyloxyphenyl)-3-((4-chlorobutoxy)methyl)-1-ethylpyrrolo[2,1,5-cd]indolizine

생성물 1

HCID 187069275-Benzyloxy-2-(4-benzyloxyphenyl)-3-((but-3-enyloxy)methyl)-1-ethylpyrrolo[2,1,5-cd]indolizine수율 52.2%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

Piperidine (0.14 g, 1.22 mmol) was dissolved in 50 ml of dry dimethylformamide under a nitrogen atmosphere and sodium hydride (60% in oil) (47 mg, 1.16 mmol) was added. The mixture was stirred for 1/2 hour. 5-Benzyloxy-2-(4-benzyloxyphenyl)-3-((4-chlorobutoxy)methyl)-1-ethylpyrrolo[2,1,5-cd ]indolizine (0.337 g, 0.583 mmol) was added and the mixture was stirred at 55-64° for 7 days. Ethanol (10 ml) was added dropwise, and the reaction mixture was diluted with 250 ml of water. The organic material was extracted into ethyl acetate (3×100 ml), and the combined organic layers were washed with brine and dried over sodium sulfate. The solvent was evaporated and the crude product was purified by column chromatography over silica gel 60, using 5% of methanol in dichloromethane as the eluent. Fractions contaiing the product wre collected to afford 165 mg (52%) of 5-benzyloxy-2-(4-benzyloxyphenyl)-3-((but-3-enyloxy)methyl)-1-ethylpyrrolo[2,1,5-cd ]indolizine as an oil. MS(SP): m/z 541 (M+). 1H-NMR (DMSO-d6, 300 MHz) δ: 1.33 (t, 3H); 2.18 (m, 2H); 3.05 (q, 2H); 3.43 (t, 2H); 4.71 (s, 2H); 4.93-5.07 (m, 2H); 5.19 (s, 2H); 5.58 (s, 2H); 5.72 (m, 1H); 7.18 (d, 2H); 7.30-7.62 (m, 14H); 7.98 (d, 1H).

후처리

  1. stirringthe mixture was stirred at 55-64° for 7 days
  2. extractionThe organic material was extracted into ethyl acetate (3×100 ml)
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was evaporated
  6. customthe crude product was purified by column chromatography over silica gel 60
  7. customcollected

출처 및 근거

ORD 기록
ord-3edd85f50c47415cac6d7d153eee44a1
출처 데이터셋
uspto-grants-2000_06
특허 번호
US06080754

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