Water → HCID 67105645, compound

HRID 1967365Notes

Reaction equation

HRID 1967365 reaction equation
[Si]([O:8][C@@H:9]1[C:13]2([CH2:15][CH2:14]2)[C:12](=[O:16])[N:11]([C:17]2[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[C:19]([Cl:25])[CH:18]=2)[C@@H:10]1[CH3:26])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1.O>C1COCC1>[Cl:25][C:19]1[CH:18]=[C:17]([N:11]2[C@H:10]([CH3:26])[C@H:9]([OH:8])[C:13]3([CH2:15][CH2:14]3)[C:12]2=[O:16])[CH:24]=[CH:23][C:20]=1[C:21]#[N:22]

Participants

5

Reactant 3

HCID 962WaterHCID 11078149TBAF tetrahydrofuranHCID 67104985HCID 67104985, compound

Product 1

HCID 67105645HCID 67105645, compoundYield 32.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of rac-4-((6R,7R)-7-(tert-butyldimethylsilyloxy)-6-methyl-4-oxo-5-azaspiro[2.4]hept-5-yl)-2-chlorobenzonitrile (140 mg) in THF (5 mL) was added tetrabutylammonium fluoride-THF solution (2.00 mL, 1 mol/L), and the mixture was stirred at room temperature for 18 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=1/0→3/1) to give the title compound as a colorless solid (yield: 32.3 mg, 32.5%).

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=1/0→3/1)

Sources & evidence

ORD record
ord-6659dd9551c9493bb4321937d23d0d67
Source dataset
uspto-grants-2013_04
Patent number
US08420694B2

Reaction notes

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