[N:1]12[CH2:8][CH2:7][C:4]([CH2:9]O)([CH2:5][CH2:6]1)[CH2:3][CH2:2]2.S([O-])(=O)(=O)C.CS(Cl)(=O)=O.[C-:21]#[N:22].[Na+]>C(Cl)(Cl)Cl.CN(C)C=O.C(N(CC)CC)C>[N:1]12[CH2:8][CH2:7][C:4]([CH2:9][C:21]#[N:22])([CH2:5][CH2:6]1)[CH2:3][CH2:2]2
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%).
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