Benzyl Bromide → 2-Benzyl-2-azabicyclo[2.2.2]octan-3-one

HRID 1896307Notes

Reaction equation

HRID 1896307 reaction equation
[CH:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C:3](=[O:9])[NH:2]2.[H-].[Na+].[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C1COCC1>[CH2:12]([N:2]1[C:3](=[O:9])[CH:4]2[CH2:7][CH2:8][CH:1]1[CH2:6][CH2:5]2)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 1378872-Azabicyclo(2.2.2)octan-3-one

Product 1

HCID 132655452-Benzyl-2-azabicyclo[2.2.2]octan-3-oneYield 47.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Compound 2-azabicyclo[2.2.2]octan-3-one (1.1 g, 8.8 mmol) in THF (10 ml) was added to a stirred suspension of sodium hydride (0.42 g, 10.6 mmol, 60%) in THF (10 ml) at 0° C. and stirred for 15 min. Benzyl bromide (1.05 ml, 8.80 mmol) was added to the reaction mixture at 0° C. and stirred for 4 h at room temperature. The reaction mixture was quenched with saturated ammonium chloride and extracted with ethyl acetate. The combined organic layer was washed with water, brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford the crude compound. The crude compound was triturated with n-pentane to afford 900 mg (47.6%) of 2-benzyl-2-aza-bicyclo[2.2.2]octan-3-one as solid.

Workup

  1. stirringstirred for 4 h at room temperature
  2. customThe reaction mixture was quenched with saturated ammonium chloride
  3. extractionextracted with ethyl acetate
  4. washThe combined organic layer was washed with water, brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto afford the crude compound
  9. customThe crude compound was triturated with n-pentane

Sources & evidence

ORD record
ord-4c900757ffac4282b11a820edecea605
Source dataset
uspto-grants-2013_08
Patent number
US08518948B2

Reaction notes

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