methyl 3-hydroxy-1-azabicyclo[2.2.2]octane-3-carboxylate

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

Procedure: Powdered 3-hydroxy-3-methoxycarbonyl-1-azabicyclo[2.2.2]octane (16.0 g, 0.086 mol) was added protionwise to thionyl chloride (100 ml) at 0°. Following the addition, the reaction mixture was stirred and heated under reflux for 48 h. The thionyl chloride was then removed under reduced pressure to afford a solid, which was recrystallised from acetone, giving 3-methoxycarbonyl-1-azabicyclo[2.2.2]oct-2-ene hydrochloride, m.p. 178°-179°. the addition heated under reflux for 48 h The thionyl chloride was then removed under reduced pressure to afford a solid, which was recrystallised from acetone

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

Procedure: 1,180 g of thionyl chloride were sufficiently cooled so that upon portionwise addition of 150 g (0.81 mole) of methyl 3-hydroxy-quinuclidine-3-carboxylate of Example 2, a temperature of 15° C. was not exceeded. Then, the mixture was refluxed for 15 hours and subsequently excess thionyl chloride was distilled off. The residue was admixed at elevated temperature with 350 ml of isopropanol, again heating at reflux. After cooling to room temperature, the suspension was filtered and the residue was washed with 80 ml of isopropanol and dried to obtain 123 g (0.61 mole) of methyl 1-azabicyclo(2,2,2)oct-2-ene-3-carboxylate hydrochloride (75% yield) having a melting point of 175° to 177° C. a temperature of 15° C. Then, the mixture was refluxed for 15 hours subsequently excess thionyl chloride was distilled off again heating at reflux the suspension was filtered the residue was washed with 80 ml of isopropanol dried

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

Procedure: Powdered 3-hydroxy-3-methoxycarbonyl-1-azabicyclo[2.2.2]octane (16.0 g, 0.086 mol) was added protionwise to thionyl chloride (100 ml) at 0°. Following the addition, the reaction mixture was stirred and heated under reflux for 48 h. The thionyl chloride was then removed under reduced pressure to afford a solid, which was recrystallised from acetone, giving 3-methoxycarbonyl-1-azabicyclo[2.2.2]oct-2-ene hydrochloride, m.p. 178°-179°. the addition heated under reflux for 48 h The thionyl chloride was then removed under reduced pressure to afford a solid, which was recrystallised from acetone

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

Procedure: Powdered 3-hydroxy-3-methoxycarbonyl-1-azabicyclo[2.2.2]octane (16.0 g, 0.086 mol) was added protionwise to thionyl chloride (100 ml) at 0°. Following the addition, the reaction mixture was stirred and heated under reflux for 48 h. The thionyl chloride was then removed under reduced pressure to afford a solid, which was recrystallised from acetone, giving 3-methoxycarbonyl-1-azabicyclo[2.2.2]oct-2-ene hydrochloride, m.p. 178°-179°. the addition heated under reflux for 48 h The thionyl chloride was then removed under reduced pressure to afford a solid, which was recrystallised from acetone