Tetrabutylammonium Fluoride → Ethyl 4-[[6-(4-hydroxy-1-piperidyl)-3-methyl-pyridine-2-carbonyl]amino]-3,5-dimethyl-benzoate

HRID 239914Notes

Reaction equation

HRID 239914 reaction equation
[Si]([O:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]2[N:20]=[C:19]([C:21]([NH:23][C:24]3[C:34]([CH3:35])=[CH:33][C:27]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:26][C:25]=3[CH3:36])=[O:22])[C:18]([CH3:37])=[CH:17][CH: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[N:20]=[C:19]([C:21]([NH:23][C:24]3[C:25]([CH3:36])=[CH:26][C:27]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:33][C:34]=3[CH3:35])=[O:22])[C:18]([CH3:37])=[CH:17][CH:16]=2)[CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86707307Ethyl 4-[[6-[4-(tert-butyl(dimethyl)silyl)oxy-1-piperidyl]-3-methyl-pyridine-2-carbonyl]amino]-3,5-dimethyl-benzoate

Product 1

HCID 86707306Ethyl 4-[[6-(4-hydroxy-1-piperidyl)-3-methyl-pyridine-2-carbonyl]amino]-3,5-dimethyl-benzoateYield 83.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of ethyl 4-[[6-[4-(tert-butyl(dimethyl)silyl)oxy-1-piperidyl]-3-methyl-pyridine-2-carbonyl]amino]-3,5-dimethyl-benzoate (342 mg, 0.650 mmol) in THF (4 ml) is added Bu4NF 1.0 M in THF (0.975 ml, 0.975 mmol) at 0° C. The reaction mixture is gradually warmed to ambient temperature. After 12 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 (223 mg, 83.3%). Mass spectrum (m/z): 412.2 (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-1104663169054221b5d3bba1e4b343a0
Source dataset
uspto-grants-2014_02
Patent number
US08642768B2

Reaction notes

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