Diisopropylamine → 1-(2-Bromo-5-((tert-butyl(dimethyl)silyl)oxy)benzyl)cyclopentanecarbonitrile

HRID 1049542Notes

Reaction equation

HRID 1049542 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.[CH:13]1([C:18]#[N:19])[CH2:17][CH2:16][CH2:15][CH2:14]1.[Br:20][C:21]1[CH:34]=[CH:33][C:24]([O:25][Si:26]([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27])=[CH:23][C:22]=1[CH2:35]Br.[Cl-].[NH4+]>C1COCC1.CCCCCC>[Br:20][C:21]1[CH:34]=[CH:33][C:24]([O:25][Si:26]([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27])=[CH:23][C:22]=1[CH2:35][C:13]1([C:18]#[N:19])[CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

8

Reactant 5

HCID 7912DiisopropylamineHCID 25517Ammonium ChlorideHCID 77935CyclopentanecarbonitrileHCID 19437125(4-Bromo-3-bromomethyl-phenoxy)-tert-butyl-dimethyl-silaneHCID 178418339Butyllithium

Product 1

HCID 1317360231-(2-Bromo-5-((tert-butyl(dimethyl)silyl)oxy)benzyl)cyclopentanecarbonitrile

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

Under a nitrogen atmosphere, to a solution of diisopropylamine (0.36 mL) in THF (7.0 mL) was added a 1.6 M solution of n-butyllithium in hexane (1.6 mL) at 0° C., and the mixture was stirred for 10 min. Cyclopentanecarbonitrile (0.28 mL) was added at −78° C., and the mixture was stirred for 30 min. A solution of (4-bromo-3-(bromomethyl)phenoxy) (tert-butyl)dimethylsilane (503 mg) in THF (3.0 mL) was added, and the mixture was stirred at −78° C. for 4 hr. To the reaction mixture was added saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (471 mg) as a colorless oil.

Workup

  1. stirringthe mixture was stirred for 30 min
  2. stirringthe mixture was stirred at −78° C. for 4 hr
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-ea8a8bd6696344aaae1e3b653a6d6dc9
Source dataset
uspto-grants-2016_07
Patent number
US09382188B2

Reaction notes

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