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

HRID 1518251Notes

Reaction equation

HRID 1518251 reaction equation
[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]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 67344093HCID 67344093, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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+).

Workup

  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

Sources & evidence

ORD record
ord-c03d82ed6d8a43a8b8ff8ec48e06a721
Source dataset
uspto-grants-2012_07
Patent number
US08232390B2

Reaction notes

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