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

HRID 239926Notes

Reaction equation

HRID 239926 reaction equation
[Si]([O:8][CH2:9][CH:10]1[CH2:15][CH2:14][CH2:13][N:12]([C:16]2[CH:17]=[CH:18][C:19]([F:37])=[C:20]([CH:36]=2)[C:21]([NH:23][C:24]2[C:33]([CH3:34])=[CH:32][C:27]([C:28]([O:30][CH3:31])=[O:29])=[CH:26][C:25]=2[CH3:35])=[O:22])[CH2:11]1)(C(C)(C)C)(C)C.[N+](CCCC)(CCCC)(CCCC)CCCC.[F-]>C1COCC1>[F:37][C:19]1[CH:18]=[CH:17][C:16]([N:12]2[CH2:13][CH2:14][CH2:15][CH:10]([CH2:9][OH:8])[CH2:11]2)=[CH:36][C:20]=1[C:21]([NH:23][C:24]1[C:33]([CH3:34])=[CH:32][C:27]([C:28]([O:30][CH3:31])=[O:29])=[CH:26][C:25]=1[CH3:35])=[O:22]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86707312Methyl 4-[[5-[3-[[tert-butyl(dimethyl)silyl]oxymethyl]-1-piperidyl]-2-fluoro-benzoyl]amino]-3,5-dimethyl-benzoate

Product 1

HCID 86707313Methyl 4-[[2-fluoro-5-[3-(hydroxymethyl)-1-piperidyl]benzoyl]amino]-3,5-dimethyl-benzoateYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of methyl 4-[[5-[3-[[tert-butyl(dimethyl)silyl]oxymethyl]-1-piperidyl]-2-fluoro-benzoyl]amino]-3,5-dimethyl-benzoate (0.30 g, 0.54 mmol) in THF (8 ml) is added Bu4NF 1.0 M in THF (0.35 g, 1.60 mmol) at 0° C. The reaction mixture is gradually warmed to ambient temperature. After 4 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 ethyl acetate in hexanes as eluent to afford the title compound as a white solid (0.10 g, 55%). Mass spectrum (m/z): 414.2 (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-e36f5437919240c0a99ce6871465990e
Source dataset
uspto-grants-2014_02
Patent number
US08642768B2

Reaction notes

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