2-(1-azabicyclo[2.2.2]octan-4-yl)acetonitrile

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Quinuclidin-4-ylmethanol (1.94 g, 0.014 moles) was converted to the corresponding mesylate by treatment with methane sulphonyl chloride and triethylamine in chloroform. The mesylate was dissolved in dimethylformamide (50 ml) and treated with sodium cyanide (1.4 g, 0.028 moles) at 120° C. for 18 hours. The mixture was cooled and concentrated in vacuo. The residue was partitioned between saturated potassium carbonate and chloroform. The organic layer was separated and dried (Na2SO4), filtered and evaporated to dryness. Chromatography on silica gel eluting with 0-10% methanol/chloroform gave the title compound 1.5 g (72%). M.S. (+ve electrospray) m/z 151 (MH+, 100%). The mixture was cooled concentrated in vacuo The residue was partitioned between saturated potassium carbonate and chloroform The organic layer was separated dried (Na2SO4) filtered evaporated to dryness

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Quinuclidin-4-ylmethanol (1.94 g, 0.014 moles) was converted to the corresponding mesylate by treatment with methane sulphonyl chloride and triethylamine in chloroform. The mesylate was dissolved in dimethylformamide (50 ml) and treated with sodium cyanide (1.4 g, 0.028 moles) at 120° C. for 18 hours. The mixture was cooled and concentrated in vacuo. The residue was partitioned between saturated potassium carbonate and chloroform. The organic layer was separated and dried (Na2SO4), filtered and evaporated to dryness. Chromatography on silica gel eluting with 0-10% methanol/chloroform gave the title compound 1.5 g (72%). M.S. (+ve electrospray) m/z 151 (MH+, 100%). The mixture was cooled concentrated in vacuo The residue was partitioned between saturated potassium carbonate and chloroform The organic layer was separated dried (Na2SO4) filtered evaporated to dryness

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 2-(Quinuclidin-4-yl)acetyl chloride may be made by converting (quinuclidin-4-yl)methanol (vide supra) to the mesylate (methanesulfonylchloride/triethylamine in chloroform) which is then treated with sodium cyanide in dimethylformamide to form (quinuclidin-4-yl)acetonitrile. Heating this in ethanol saturated with hydrogen chloride gas produces the corresponding ethyl ester which is hydrolyzed to the acid by treatment with 6N hydrochloric acid. Finally, the acid is converted to the acid chloride as described above.