Water → HCID 21564945, compound

Participants

Reaction Steps

0.17 g of lithium is added to 8 ml of absolute ether in a nitrogen atmosphere, and a solution of 1.6 g of methyl iodide in 3 ml of absolute ether is added dropwise thereto at 0° to -5°C. The mixture is stirred at the same temperature for 30 minutes. Then, a solution of 1.0 g of 1-(3-methoxyphenyl)-6-methyl-6-azabicyclo[3,2,1]octane-7-one in 30 ml of benzene is added dropwise to the mixture at room temperature for 5 minutes. The mixture is refluxed for 3 hours. Water is added to the mixture under ice-cooling, and the aqueous mixture is extracted with ether. The ether extract is washed with water, dried and then evaporated to remove solvent, whereby 1.0 g of 1-(3-methoxyphenyl)-6-methyl-7-methylidene-6-azabicyclo[3,2,1]octane is obtained. The product thus obtained is dissolved in 60 ml of ethanol. 300 mg of sodium borohydride are added to the ethanol solution at 10° to 15°C. Then, the mixture is stirred at room temperature for 20 hours. After the reaction, the mixture is concentrated under reduced pressure. Water is added to the residue, and the aqueous mixture is extracted with chloroform. The chloroform extract is washed with water, dried and then evaporated to remove solvent. Methanolic hydrogen bromide is added to the residue in ether, and the crystalline precipitate is collected by filtration. The precipitate is recrystallized from a mixture of ethanol, acetone and ether. 1.1 g of 1-(3-methoxyphenyl)-6,7-dimethyl-6-azabicyclo[3,2,1]octane hydrobromide are obtained. M.p. 175° - 177°C.

Provenance & Evidence