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Water → 2-fluoro-4-[(2S,3S)-3-hydroxy-2-methyl-5-oxopyrrolidin-1-yl]-3-methylbenzonitrile

HRID 1173658
Notes
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Reaction equation

HRID 1173658 reaction equation
[Si]([O:8][C@H:9]1[CH2:13][C:12](=[O:14])[N:11]([C:15]2[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[C:17]([F:23])[C:16]=2[CH3:24])[C@H:10]1[CH3:25])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1.O>C1COCC1>[F:23][C:17]1[C:16]([CH3:24])=[C:15]([N:11]2[C:12](=[O:14])[CH2:13][C@H:9]([OH:8])[C@@H:10]2[CH3:25])[CH:22]=[CH:21][C:18]=1[C:19]#[N:20]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962WaterHCID 11078149TBAF tetrahydrofuranHCID 595569304-[(2S,3S)-3-(tert-butyldimethylsilyloxy)-2-methyl-5-oxopyrrolidin-1-yl]-2-fluoro-3-methylbenzonitrile

Product 1

HCID 595568872-fluoro-4-[(2S,3S)-3-hydroxy-2-methyl-5-oxopyrrolidin-1-yl]-3-methylbenzonitrileYield 62%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

To a solution of 4-[(2S,3S)-3-(tert-butyldimethylsilyloxy)-2-methyl-5-oxopyrrolidin-1-yl]-2-fluoro-3-methylbenzonitrile (330 mg) in THF (10 mL) was added tetrabutylammonium fluoride-THF solution (1.18 mL, 1 mol/L), and the mixture was stirred at room temperature for 5 hr. The reaction mixture was added to water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography, and recrystallized from hexane-ethyl acetate to give the title compound as a colorless solid (yield: 139 mg, 62%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography
  6. customrecrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-fc15a1de10af4b3685a1575cd0fc4f86
Source dataset
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07834051B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes