1-azabicyclo[2.2.2]oct-3-yl methanesulfonate

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The procedure described in preparation 6-(2) was repeated, but using 3.7 g of 3-methanesulfonyloxyquinuclidine (prepared by the methanesulfonylation of 3-quinuclidinol), 3.0 ml of 4-methoxybenzyl mercaptan and 0.942 g of sodium hydride (as a 55% w/w suspension in mineral oil), to afford 1.74 g of the title compound as an oil. The procedure described in preparation 6-(2)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The procedure described in Preparation 6-(2) was repeated, but using 3.7 g of 3-methanesulfonyloxyquinuclidine (prepared by the methanesulfonylation of 3-quinuclidinol), 3.0 ml of 4-methoxybenzyl mercaptan and 0.942 g of sodium hydride (as a 55% w/w suspension in mineral oil), to afford 1.74 g of the title compound as an oil. The procedure described in Preparation

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The procedure described in Preparation 6-(2) was repeated, but using 3.7 g of 3-methanesulfonyloxyquinuclidine (prepared by the methanesulfonylation of 3-quinuclidinol), 3.0 ml of 4-methoxybenzyl mercaptan and 0.942 g of sodium hydride (as a 55% w/w suspension in mineral oil), to afford 1.74 g of the title compound as an oil. The procedure described in Preparation

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3-Methanesulphonyloxy-1-azabicylo[2.2.2]octane (D8) (2.0 g, 9.7 mmol) and the sodium salt of 5-aminotetrazole (D15) (2.5 g, 2.0 eq) were dissolved in dry DMF (50 ml) and the reaction carried out as for Example 10. The product (E11) isolated from column chromatography was a white crystalline solid (124 mg, 6.6%), which was recrystallised from ether, m.p. 132-134° C. The product (E11) isolated from column chromatography was recrystallised from ether, m.p. 132-134° C.

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Quinuclidin-3-ol (10.0 g, 0.0787 mol) was dissolved under N2 in dry dichloromethane (200 ml) and cooled in an ice bath to 0° C. Methanesulphonyl chloride (7.3 ml, 10.8 g, 0.094 mol, 1.2 eq) and dry pyridine (7.64 ml, 7.46 g, 0.094 mol, 1.2 eq) were added and the mixture stirred at 0° C. for 20 min. The solution was then warmed to r.t. and stirred under N2 for 1 h. Saturated aqueous potassium carbonate solution (150 ml) was added, and the organic layer extracted and collected. The aqueous layer was re-extracted with EtOAc (3×200 ml), the organic solutions dried (Na2SO4), filtered, and evaporated to dryness under reduced pressure to yield a pale yellow oil which was pumped under high vacuum to remove any last traces of pyridine to yield the title compound (D8) (15.8 g, 98%). The solution was then warmed to r.t. stirred under N2 for 1 h the organic layer extracted collected The aqueous layer was re-extracted with EtOAc (3×200 ml) the organic solutions dried (Na2SO4) filtered evaporated to dryness under reduced pressure to yield a pale yellow oil which to remove any last traces of pyridine

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The procedure described in preparation 6-(2) was repeated, but using 3.7 g of 3-methanesulfonyloxyquinuclidine (prepared by the methanesulfonylation of 3-quinuclidinol), 3.0 ml of 4-methoxybenzyl mercaptan and 0.942 g of sodium hydride (as a 55% w/w suspension in mineral oil), to afford 1.74 g of the title compound as an oil. The procedure described in preparation 6-(2)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The procedure described in Preparation 6-(2) was repeated, but using 3.7 g of 3-methanesulfonyloxyquinuclidine (prepared by the methanesulfonylation of 3-quinuclidinol), 3.0 ml of 4-methoxybenzyl mercaptan and 0.942 g of sodium hydride (as a 55% w/w suspension in mineral oil), to afford 1.74 g of the title compound as an oil. The procedure described in Preparation