Tetrabutylammonium Fluoride → HCID 59381926, compound

HRID 2354568Notes

Reaction equation

HRID 2354568 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[C:16]3[C:20](=[CH:21][CH:22]=2)[N:19]([Si](C(C)(C)C)(C)C)[CH:18]=[CH:17]3)[CH:10]([CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[C:16]3[C:20](=[CH:21][CH:22]=2)[NH:19][CH:18]=[CH:17]3)[CH:10]([CH2:30][C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 59381924HCID 59381924, compound

Product 1

HCID 59381926HCID 59381926, compoundYield 93.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of 3-benzyl-4-[1-(tert-butyl-dimethyl-silanyl)-1H-indol-5-yl]-piperazine-1-carboxylic acid tert-butyl ester (1.61 g, 3.2 mmol) in 20 mL THF at 0° C. was added TBAF (3.5 mL, 1.0 M in THF, 3.5 mmol). After 15 minutes the solution was quenched by the addition of water, concentrated under reduced pressure, and extracted with ethyl acetate. The combined organic layers were washed with water and brine, dried over Na2SO4, filtered and concentrated under reduced pressure. Purification via flash chromatography (5% to 40% EtOAc in hexanes) afforded 3-benzyl-4-(1H-indol-5-yl)-piperazine-1-carboxylic acid tert-butyl ester (1.17 g, 93%) as a white foam; MS (M+H)=392.

Workup

  1. customAfter 15 minutes the solution was quenched by the addition of water
  2. concentrationconcentrated under reduced pressure
  3. extractionextracted with ethyl acetate
  4. washThe combined organic layers were washed with water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customPurification via flash chromatography (5% to 40% EtOAc in hexanes)

Sources & evidence

ORD record
ord-af8d1169dae749ac8a1464d23aaf83cf
Source dataset
uspto-grants-2010_07
Patent number
US07754721B2

Reaction notes

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