Tetrabutylammonium Fluoride → HCID 86641264, compound

HRID 1690781Notes

Reaction equation

HRID 1690781 reaction equation
[CH:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([S:11](CC[Si](C)(C)C)(=[O:13])=[O:12])=[CH:7][C:6]=1[C:20]([N:22]1[CH2:30][C:29]2[C:24](=[CH:25][CH:26]=[C:27]([CH:31]3[CH2:36][CH2:35][O:34][CH2:33][CH2:32]3)[CH:28]=2)[CH2:23]1)=[O:21])([CH3:3])[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-].C(O)(=O)CC(CC(O)=O)(C(O)=O)O.[Na+:68].[Cl-]>C1COCC1>[Na+:68].[CH:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([O-:13])=[O:12])=[CH:7][C:6]=1[C:20]([N:22]1[CH2:30][C:29]2[C:24](=[CH:25][CH:26]=[C:27]([CH:31]3[CH2:32][CH2:33][O:34][CH2:35][CH2:36]3)[CH:28]=2)[CH2:23]1)=[O:21])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 2724141Tetrabutylammonium FluorideHCID 23675227HCID 23675227, compoundHCID 59309386HCID 59309386, compound

Product 1

HCID 86641264HCID 86641264, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1.40 g (2.64 mmol) of [2-isopropoxy-5-(2-trimethylsilanyl-ethanesulfonyl)-phenyl]-[5-(tetrahydro-pyran-4-yl)-1,3-dihydro-isoindol-2-yl]-methanone was dissolved in 14 ml of THF and treated with 4.0 ml (4.0 mmol) of a 1 M solution of TBAF in THF at 60° C. during 3.5 hours. The reaction mixture was poured on an aqueous solution of citric acid/NaCl, then extracted with MTBE/THF 1:1. The organic solvent was evaporated, the residue was dissolved in MeOH/water (3:1) and treated with 600 mg of NaHCO3. After evaporation, the residue was purified chromatographically on a reverse phase column (RP-18, water/methanol) to provide 0.66 g (55%) of the title compound as a white foam. MS (m/e): 430.2 [M+H]+.

Workup

  1. extractionextracted with MTBE/THF 1:1
  2. customThe organic solvent was evaporated
  3. dissolutionthe residue was dissolved in MeOH/water (3:1)
  4. additiontreated with 600 mg of NaHCO3
  5. customAfter evaporation
  6. customthe residue was purified chromatographically on a reverse phase column (RP-18, water/methanol)

Sources & evidence

ORD record
ord-38bb629419ae4783a2d3f10e36c695f3
Source dataset
uspto-grants-2012_04
Patent number
US08153679B2

Reaction notes

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