Tetrabutylammonium Fluoride → methyl 1-allyl-3-cyclohexyl-2-[2-(hydroxymethyl)-4-methoxyphenyl]-1H-indole-6-carboxylate

HRID 1518251노트

반응식

HRID 1518251 반응식
[CH2:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:13]([O:15][CH3:16])=[O:14])[CH:11]=2)[C:6]([CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)=[C:5]1[C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][C:24]=1[CH2:31][O:32][Si](C(C)C)(C(C)C)C(C)C)[CH:2]=[CH2:3].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH2:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:13]([O:15][CH3:16])=[O:14])[CH:11]=2)[C:6]([CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)=[C:5]1[C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][C:24]=1[CH2:31][OH:32])[CH:2]=[CH2:3]

참가 물질

4

반응물 2

HCID 2724141Tetrabutylammonium FluorideHCID 67344093HCID 67344093, 화합물

생성물 1

HCID 67345867methyl 1-allyl-3-cyclohexyl-2-[2-(hydroxymethyl)-4-methoxyphenyl]-1H-indole-6-carboxylate수율 88%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

Methyl 1-allyl-3-cyclohexyl-2-(4-methoxy-2-{[(triisopropylsilyl)oxy]methyl}phenyl)-1H-indole-6-carboxylate (1 eq.) was dissolved in THF (0.28M solution) and a 1M solution of tetrabutylammonium fluoride in THF (1 eq.) was added. The mixture was left stirring at RT for 2 h, then all volatiles were evaporated in vacuo and the residual material was dissolved in Et2O. The solution was washed with 1N HCl, saturated aq. NaHCO3 solution and with brine. The organic phase was dried over Na2SO4 and evaporated in vacuo. The residual material was purified by flash chromatography (PE:EtOAc, 8:2). After evaporation of the solvents the product was obtained as colorless foam (88%). MS (ES+): 434.2 (M+H+).

후처리

  1. waitThe mixture was left
  2. customall volatiles were evaporated in vacuo
  3. dissolutionthe residual material was dissolved in Et2O
  4. washThe solution was washed with 1N HCl, saturated aq. NaHCO3 solution and with brine
  5. dry with materialThe organic phase was dried over Na2SO4
  6. customevaporated in vacuo
  7. customThe residual material was purified by flash chromatography (PE:EtOAc, 8:2)
  8. customAfter evaporation of the solvents the product

출처 및 근거

ORD 기록
ord-c03d82ed6d8a43a8b8ff8ec48e06a721
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08232390B2

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