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

HRID 239941Notes

Reaction equation

HRID 239941 reaction equation
[Si]([O:8][CH2:9][CH:10]1[CH2:14][CH2:13][N:12]([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])[CH2:11]1)(C(C)(C)C)(C)C.[N+](CCCC)(CCCC)(CCCC)CCCC.[F-]>C1COCC1>[OH:8][CH2:9][CH:10]1[CH2:14][CH2:13][N:12]([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])[CH2:11]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86707328Methyl 3-[[5-[3-[[tert-butyl(dimethyl)silyl]oxymethyl]pyrrolidin-1-yl]-2-methyl-benzoyl]amino]-2,4-dimethyl-benzoate

Product 1

HCID 86707327Methyl 3-[[5-[3-(hydroxymethyl)pyrrolidin-1-yl]-2-methyl-benzoyl]amino]-2,4-dimethyl-benzoateYield 55.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of methyl 3-[[5-[3-[[tert-butyl(dimethyl)silyl]oxymethyl]pyrrolidin-1-yl]-2-methyl-benzoyl]amino]-2,4-dimethyl-benzoate (0.35 g, 0.686 mmol) in THF (50 ml) is added Bu4NF 1.0 M in THF (0.537 g, 2.05 mmol) at 0° C. The reaction mixture is gradually warmed to ambient temperature. After 2 hours, 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 50% ethyl acetate in hexane to afford the title compound as a brown solid (150 mg, 51%).

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-5ddbf9008721457cb231e04164dae99a
Source dataset
uspto-grants-2014_02
Patent number
US08642768B2

Reaction notes

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