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

HRID 239988Notes

Reaction equation

HRID 239988 reaction equation
[Si]([O:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]2[CH:16]=[C:17]([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:18]3[C:23]([CH:24]=2)=[CH:22][CH:21]=[CH:20][CH:19]=3)[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:16]=[C:17]([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:18]3[C:23]([CH:24]=2)=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:13][CH2:14]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86707372Methyl 3-[[3-[4-[tert-butyl(dimethyl)silyl]oxy-1-piperidyl]naphthalene-1-carbonyl]amino]-2,4-dimethyl-benzoate

Product 1

HCID 86707373Methyl 3-[[3-(4-hydroxy-1-piperidyl)naphthalene-1-carbonyl]amino]-2,4-dimethyl-benzoateYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of methyl 3-[[3-[4-[tert-butyl(dimethyl)silyl]oxy-1-piperidyl]naphthalene-1-carbonyl]amino]-2,4-dimethyl-benzoate (0.30 g, 0.54 mmol) in THF (8.0 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 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 white solid (0.10 g, 55%). Mass spectrum (m/z): 433.0 (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-6480cadab9a5493db1d9aed269ff06c1
Source dataset
uspto-grants-2014_02
Patent number
US08642768B2

Reaction notes

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