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

HRID 1422086ノート

反応式

HRID 1422086 の反応式
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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-3edd85f50c47415cac6d7d153eee44a1
出典データセット
uspto-grants-2000_06
特許番号
US06080754

反応ノート

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