Acetyl chloride → 5-Benzyloxy-2-(4-benzyloxyphenyl)-1-ethyl-4-(1-oxo-3-piperidinopropyl)pyrrolo[2,1,5-cd]indolizine

HRID 1422097

反応式

HRID 1422097 の反応式
N1([CH2:7][N:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)CCCCC1.C(Cl)(=O)C.[C:18]([C:21]1[CH:22]=[C:23]2[N:31]3[C:26](=[CH:27][CH:28]=[C:29]([O:32][CH2:33][C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[C:30]=13)[C:25]([CH2:40][CH3:41])=[C:24]2[C:42]1[CH:47]=[CH:46][C:45]([O:48][CH2:49][C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)=[CH:44][CH:43]=1)(=[O:20])[CH3:19]>C(COC)OC>[CH2:33]([O:32][C:29]1[C:30]2[N:31]3[C:26](=[CH:27][CH:28]=1)[C:25]([CH2:40][CH3:41])=[C:24]([C:42]1[CH:47]=[CH:46][C:45]([O:48][CH2:49][C:50]4[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=4)=[CH:44][CH:43]=1)[C:23]3=[CH:22][C:21]=2[C:18](=[O:20])[CH2:19][CH2:7][N:8]1[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

参加物

5

反応物 3

HCID 6367Acetyl chlorideHCID 70151DipiperidinomethaneHCID 187070344-Acetyl-5-benzyloxy-2-(4benzyloxyphenyl)-1-ethylpyrrolo[2,1,5-cd]indolizine

生成物 1

HCID 187070135-Benzyloxy-2-(4-benzyloxyphenyl)-1-ethyl-4-(1-oxo-3-piperidinopropyl)pyrrolo[2,1,5-cd]indolizine収率 28.5%

試薬・触媒・溶媒 1

HCID 80711,2-Dimethoxyethane溶媒

実験手順

Dipiperidinomethane (0.3 ml, 1.5 mmol) was dissolved in 20 ml of dimethoxyethane and acetyl chloride (0.11 ml, 1.5 mmol) was added. The mixture was stirred for 30 minutes, while 4-acetyl-5-benzyloxy-2-(4benzyloxyphenyl)-1-ethylpyrrolo[2,1,5-cd]indolizine (0.5 g, 1.0 mmol) was added and HCl-gas was bubbled through the mixture for 15 minutes. The reaction mixture was refluxed for 5 hours and stirred at room temperature for 16 hours. The solvent was evaporated, and the crude HCl-salt was purified by column chromatography over silica gel 60, using 5% of methanol in dichloromethane as the eluent. Fractions containing the HCl-salt were combined and the solvent was evaporated. The salt was dissolved in 20 ml of dry dichloromethane and 2.13 g sodium sulfate and 2.76 g potassium carbonate was added. The mixture was stirred at room temperature for 24 hours. Remaining salts were filtered off, and the solvent was evaporated. The crude product was purified by column chromatography over silica gel 60, using 5% methanol in dichloromethane as the eluent to afford 170 mg (28%) of 5-benzyloxy-2-(4-benzyloxyphenyl)-1-ethyl-4-(1-oxo-3-piperidinopropyl)pyrrolo[2,1,5-cd]indolizine as an oil. 1H--NMR (CDCl3, 200 MHz) δ: 1.35-1.75 (m, 9 H); 2.34-3.75 (m, 10 H); 5.17 (s, 4 H); 7.10-7.78 (m, 17 H).

後処理

  1. additionwas added
  2. customHCl-gas was bubbled through the mixture for 15 minutes
  3. temperatureThe reaction mixture was refluxed for 5 hours
  4. customThe solvent was evaporated
  5. customthe crude HCl-salt was purified by column chromatography over silica gel 60
  6. additionFractions containing the HCl-salt
  7. customthe solvent was evaporated
  8. dissolutionThe salt was dissolved in 20 ml of dry dichloromethane
  9. addition2.13 g sodium sulfate and 2.76 g potassium carbonate was added
  10. stirringThe mixture was stirred at room temperature for 24 hours
  11. filtrationRemaining salts were filtered off
  12. customthe solvent was evaporated
  13. customThe crude product was purified by column chromatography over silica gel 60

出典と根拠

ORDレコード
ord-088d187dc82643288b9e2c2bad86f09f
出典データセット
uspto-grants-2000_06
特許番号
US06080754

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