Thionyl Chloride → Methyl 1-azabicyclo[2.2.2]oct-2-ene-3-carboxylate--hydrogen chloride (1/1)

Participants

Reaction Steps

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.

Provenance & Evidence