Tetrabutylammonium Fluoride → Methyl 4-[[2-(4-Hydroxy-1-Piperidyl)Quinoline-4-carbonyl]Amino]-3,5-dimethyl-benzoate

HRID 239980Notes

Reaction equation

HRID 239980 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:37]([CH3:38])=[CH:36][C:31]([C:32]([O:34][CH3:35])=[O:33])=[CH:30][C:29]=3[CH3:39])=[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[CH2:10][CH2:11][N:12]([C:15]2[CH:24]=[C:23]([C:25]([NH:27][C:28]3[C:29]([CH3:39])=[CH:30][C:31]([C:32]([O:34][CH3:35])=[O:33])=[CH:36][C:37]=3[CH3:38])=[O:26])[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]=2)[CH2:13][CH2:14]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86707364Methyl 4-(2-(4-((tert-butyldimethylsilyl)oxy)piperidin-1-yl)quinoline-4-carboxamido)-3,5-dimethylbenzoate

Product 1

HCID 86707365Methyl 4-[[2-(4-Hydroxy-1-Piperidyl)Quinoline-4-carbonyl]Amino]-3,5-dimethyl-benzoateYield 78.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of methyl 4-(2-(4-((tert-butyldimethylsilyl)oxy)piperidin-1-yl)quinoline-4-carboxamido)-3,5-dimethylbenzoate (0.21 g, 0.00038 mol) in THF (4 ml) is added Bu4NF 1.0 M in THF (4.0 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) over a gradient using 0-40% ethyl acetate in hexanes to afford the title compound as a light yellow solid (0.13 g, 78%). Mass spectrum (m/z): 434.2 (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-e73293fdba2f4825a74fcb9b668d1c4d
Source dataset
uspto-grants-2014_02
Patent number
US08642768B2

Reaction notes

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