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

HRID 239944Notes

Reaction equation

HRID 239944 reaction equation
[Si]([O:8][CH:9]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[CH:16]=[CH:17][C:18]([CH3:36])=[C:19]([CH:35]=2)[C:20]([NH:22][C:23]2[C:24]([CH3:34])=[C:25]([CH:30]=[CH:31][C:32]=2[CH3:33])[C:26]([O:28][CH3:29])=[O:27])=[O:21])[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][CH2:12][N:11]([C:15]2[CH:16]=[CH:17][C:18]([CH3:36])=[C:19]([CH:35]=2)[C:20]([NH:22][C:23]2[C:24]([CH3:34])=[C:25]([CH:30]=[CH:31][C:32]=2[CH3:33])[C:26]([O:28][CH3:29])=[O:27])=[O:21])[CH2:10]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86707330Methyl 3-[[5-[3-[tert-butyl(dimethyl)silyl]oxy-1-piperidyl]-2-methyl-benzoyl]amino]-2,4-dimethyl-benzoate

Product 1

HCID 86707331Methyl 3-[[5-(3-hydroxy-1-piperidyl)-2-methyl-benzoyl]amino]-2,4-dimethyl-benzoateYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of methyl 3-[[5-[3-[tert-butyl(dimethyl)silyl]oxy-1-piperidyl]-2-methyl-benzoyl]amino]-2,4-dimethyl-benzoate (0.4 g, 0.78 mmol) in THF (20 ml) is added Bu4NF 1.0 M in THF (0.409 g, 1.56 mmol) at 0° C. The reaction mixture is gradually warmed to ambient temperature. After 1 hour, the reaction mixture is diluted with ice-water and extracted twice 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 3% methanol in dichloromethane to afford the title compound as a white solid (0.3 g, 97%).

Workup

  1. extractionextracted twice 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-f8906d407e5e490289d86760dd5f06ff
Source dataset
uspto-grants-2014_02
Patent number
US08642768B2

Reaction notes

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