Tetrabutylammonium Fluoride → Methyl 3-[[2-(4-hydroxy-1-piperidyl)quinoline-4-carbonyl]amino]-2,4-dimethyl-benzoate

HRID 239984Notes

Reaction equation

HRID 239984 reaction equation
[Si]([O:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]2[CH:24]=[C:23]([C:25]([NH:27][C:28]3[C:29]([CH3:39])=[C:30]([CH:35]=[CH:36][C:37]=3[CH3:38])[C:31]([O:33][CH3:34])=[O:32])=[O:26])[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]=2)[CH2:11][CH2:10]1)(C(C)(C)C)(C)C.[N+](CCCC)(CCCC)(CCCC)CCCC.[F-]>C1COCC1>[OH:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]2[CH:24]=[C:23]([C:25]([NH:27][C:28]3[C:29]([CH3:39])=[C:30]([CH:35]=[CH:36][C:37]=3[CH3:38])[C:31]([O:33][CH3:34])=[O:32])=[O:26])[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]=2)[CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86707368Methyl 3-(2-(4-((tert-butyldimethylsilyl)oxy)piperidin-1-yl)quinoline-4-carboxamido)-2,4-dimethylbenzoate

Product 1

HCID 86707369Methyl 3-[[2-(4-hydroxy-1-piperidyl)quinoline-4-carbonyl]amino]-2,4-dimethyl-benzoateYield 27%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of methyl 3-(2-(4-((tert-butyldimethylsilyl)oxy)piperidin-1-yl)quinoline-4-carboxamido)-2,4-dimethylbenzoate (1.30 g, 0.00087 mol) in THF (2.0 ml) is added Bu4NF 1.0 M in THF (10.0 ml) at 0° C. The reaction mixture is gradually warmed to ambient temperature. After 14 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) with ethyl acetate in hexanes to afford the title compound as a yellow solid (0.10 g, 27%). Mass spectrum (m/z): 434.3 (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) with ethyl acetate in hexanes

Sources & evidence

ORD record
ord-48375aa947524c86ae5729367f971b77
Source dataset
uspto-grants-2014_02
Patent number
US08642768B2

Reaction notes

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