Ethanol → 8-Benzyl-8-azabicyclo[3.2.1]octane-3-carbonitrile

HRID 1368175Notes

Reaction equation

HRID 1368175 reaction equation
CC(C)([O-])C.[K+].[CH2:7]([N:14]1[CH:19]2[CH2:20][CH2:21][CH:15]1[CH2:16][C:17](=O)[CH2:18]2)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.S([CH2:33][N+:34]#[C-])(C1C=CC(C)=CC=1)(=O)=O.C(O)C>C(COC)OC>[C:33]([CH:17]1[CH2:16][CH:15]2[N:14]([CH2:7][C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH:19]([CH2:20][CH2:21]2)[CH2:18]1)#[N:34]

Participants

6

Reactant 4

HCID 702EthanolHCID 1198468-Benzyl-8-azabicyclo(3.2.1)octan-3-oneHCID 161915Tosylmethyl isocyanideHCID 23665647Potassium tert-butoxide

Product 1

HCID 221357008-Benzyl-8-azabicyclo[3.2.1]octane-3-carbonitrileYield 41.4%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

Potassium t-butoxide (2.5 g) was added portionwise to a stirred mixture of 8-benzyl-8-azabicyclo[3.2.1]octan-3-one (2.0 g), tosylmethyl isocyanide (2.36 g) and ethanol (2 ml) in dimethoxyethane (50 ml) at 0° C. under nitrogen. The mixture was stifled at 0° C. for 0.5 hours and then overnight at room temperature. The mixture was then filtered and the solid residue washed with dimethoxyethane. The combined filtrates were evaporated under reduced pressure and chromatographed [SiO2; hexane:ethyl acetate (80:20)] to give 3-cyano-8-benzyl-8-azabicyclo[3.2.1]octane (0.87 g).

Workup

  1. customovernight
  2. customat room temperature
  3. filtrationThe mixture was then filtered
  4. washthe solid residue washed with dimethoxyethane
  5. customThe combined filtrates were evaporated under reduced pressure
  6. customchromatographed [SiO2; hexane:ethyl acetate (80:20)]

Sources & evidence

ORD record
ord-d3c4e46798e24d3cb16b577a69dbe489
Source dataset
uspto-grants-2003_06
Patent number
US06573275B1

Reaction notes

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