Water → HCID 59556875, compound

HRID 1967366Notes

Reaction equation

HRID 1967366 reaction equation
[Si]([O:8][C@@H:9]1[C@H:13]([CH3:14])[N:12]([C:15]2[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[C:17]([C:23]([F:26])([F:25])[F:24])[CH:16]=2)[C:11](=[O:27])[C:10]1([CH3:29])[CH3:28])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1.O>C1COCC1>[OH:8][C@@H:9]1[C@H:13]([CH3:14])[N:12]([C:15]2[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[C:17]([C:23]([F:24])([F:25])[F:26])[CH:16]=2)[C:11](=[O:27])[C:10]1([CH3:28])[CH3:29]

Participants

5

Reactant 3

HCID 962WaterHCID 11078149TBAF tetrahydrofuranHCID 59557006HCID 59557006, compound

Product 1

HCID 59556875HCID 59556875, compoundYield 22.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-((4S,5S)-4-(tert-butyldimethylsilyloxy)-3,3,5-trimethyl-2-oxopyrrolidin-1-yl)-2-(trifluoromethyl)benzonitrile (232.2 mg) in THF (6 mL) was added tetrabutylammonium fluoride-THF solution (2.0 mL, 1 mol/L), and the mixture was stirred at room temperature for 1 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 (eluent: hexane/ethyl acetate=30/1→1/3), and recrystallized from hexane-ethyl acetate to give the title compound as a colorless solid (yield: 38.9 mg, 22.9%).

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 (eluent: hexane/ethyl acetate=30/1→1/3)
  6. customrecrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-f12d2ccf30934d6d9dcdd51c855f2e72
Source dataset
uspto-grants-2013_04
Patent number
US08420694B2

Reaction notes

Loading…