Tetrabutylammonium Fluoride → Methyl 4-[[5-(4-hydroxy-1-piperidyl)-2-(trifluoromethyl)benzoyl]amino]-3,5-dimethyl-benzoate

HRID 239994Notes

Reaction equation

HRID 239994 reaction equation
[Si]([O:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]2[CH:16]=[CH:17][C:18]([C:36]([F:39])([F:38])[F:37])=[C:19]([CH:35]=2)[C:20]([NH:22][C:23]2[C:32]([CH3:33])=[CH:31][C:26]([C:27]([O:29][CH3:30])=[O:28])=[CH:25][C:24]=2[CH3:34])=[O:21])[CH2:11][CH2:10]1)(C(C)(C)C)(C)C.[N+](CCCC)(CCCC)(CCCC)CCCC.[F-]>C1COCC1>[OH:8][CH:9]1[CH2:10][CH2:11][N:12]([C:15]2[CH:16]=[CH:17][C:18]([C:36]([F:39])([F:37])[F:38])=[C:19]([CH:35]=2)[C:20]([NH:22][C:23]2[C:24]([CH3:34])=[CH:25][C:26]([C:27]([O:29][CH3:30])=[O:28])=[CH:31][C:32]=2[CH3:33])=[O:21])[CH2:13][CH2:14]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86707379Methyl 4-[[5-[4-[tert-butyl(dimethyl)silyl]oxy-1-piperidyl]-2-(trifluoromethyl)benzoyl]amino]-3,5-dimethyl-benzoate

Product 1

HCID 86707380Methyl 4-[[5-(4-hydroxy-1-piperidyl)-2-(trifluoromethyl)benzoyl]amino]-3,5-dimethyl-benzoateYield 81.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of methyl 4-[[5-[4-[tert-butyl(dimethyl)silyl]oxy-1-piperidyl]-2-(trifluoromethyl)benzoyl]amino]-3,5-dimethyl-benzoate (0.10 g, 177.08 moles) in THF (4 ml) is added Bu4NF 1.0 M in THF (1.0 ml) at 0° C. The reaction mixture is gradually warmed to ambient temperature. After 6 hours, the reaction mixture is diluted with ice-water and extracted with ethyl acetate. The organic layers are combined, dried over sodium sulfate, filtered, and concentrated under reduced pressure to give a residue. The residue is purified by flash chromatography (silica gel) over a gradient using 40-60% ethyl acetate in hexanes to afford the title compound as a light yellow solid (0.06 g, 81.5%). Mass spectrum (m/z): 451.2 (M+1).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customto give a residue
  6. customThe residue is purified by flash chromatography (silica gel) over a gradient

Sources & evidence

ORD record
ord-95a93e01410843de89b06522af721e3b
Source dataset
uspto-grants-2014_02
Patent number
US08642768B2

Reaction notes

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