Tetrabutylammonium Fluoride → HCID 67265117, compound

HRID 1685149Notes

Reaction equation

HRID 1685149 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[N:15]([CH2:27][CH2:28][O:29][Si](C(C)(C)C)(C)C)[CH:16]=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[C:21]([F:26])[CH:20]=3)[N:18]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[N:15]([CH2:27][CH2:28][OH:29])[CH:16]=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[C:21]([F:26])[CH:20]=3)[N:18]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 67265143HCID 67265143, compound

Product 1

HCID 67265117HCID 67265117, compoundYield 24.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Combine 4-[1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-(3,4-difluoro-phenyl)-1H-imidazol-2-yl]-piperidine-1-carboxylic acid tert-butyl ester (18.3 g; 0.035 mol; 1.0 equiv), tetrabutylammonium fluoride (20.3 g; 0.07 mol; 2.0 equiv) in THF (100 mL) and stir at RT for 3 h. Concentrate, quench the reaction with water and extract with EA. Evaporate the organic layer to give the title compound (3.5 g; 24.49%). MS (ES+): m/z=408(M+H).

Workup

  1. concentrationConcentrate
  2. customquench
  3. customthe reaction with water
  4. extractionextract with EA
  5. customEvaporate the organic layer

Sources & evidence

ORD record
ord-f9247424e85c4c4c9fe200c533c32129
Source dataset
uspto-grants-2012_04
Patent number
US08148387B2

Reaction notes

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