Carbon Dioxide → 3-Chloro-8-methyl-8-azabicyclo(3.2.1)octane

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Reaction Steps

To a solution of 95 g pseudotropine in 420 ml abs. CHCl3 are added dropwise at 0° 195 ml thionyl chloride within 20 minutes. The reaction mixture is refluxed for 4 hours, then left overnight at room temperature and then heated to 60°-65° for 3 hours. The mixture is then diluted with CH2Cl2 to a volume of ca. 100 to 150 ml and poured on ice-water. A 35% aqueous NaOH solution is added to a pH 11 and then dry ice to a pH 10. After extraction with CH2Cl2 and distillation of the extracts (second fraction~97°-98°) the title compound is obtained.

Provenance & Evidence