[CH:1]12[CH2:9][CH:5]([CH2:6][CH2:7][CH2:8]1)[CH2:4][CH2:3][NH:2]2.[CH2:10](Br)[CH:11]=[CH2:12].C(=O)([O-])[O-].[K+].[K+].CCOCC>C(COC)OC>[CH2:12]([N:2]1[CH2:3][CH2:4][CH:5]2[CH2:9][CH:1]1[CH2:8][CH2:7][CH2:6]2)[CH:11]=[CH2:10]To a solution (6.5 ml) of 2-azabicyclo[3.3.1]nonane (100 mg, 0.62 mmol) in dimethoxyethane were added allylbromide (105 mg, 0.87 mmol) and potassium carbonate (94 mg, 0.68 mmol) and the mixture was heated at reflux temperature for 3.5 hours. Ether (10 ml) was added to the reaction mixture, followed by filtration and removal of the solvent, and the residue was purified with silica gel column chromatography (chloroform-methanol-triethylamine=100:9:1), to obtain 2-allyl-2-azabicyclo[3.3.1]nonane (52 mg, 51%) as a colorless oily substance.
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