The Preparation of 2‐Arylmethylidene‐8‐methyl‐8‐azabicyclo[3.2.1]octan‐3‐ones

Abstract

An efficient and versatile two‐step synthesis of 2‐arylmethylidene‐8‐methyl‐8‐azabicyclo[3.2.1]octane‐3‐ones, via mono aldol condensation of tropinone with a variety of aryl aldehydes followed by pTsOH‐catalyzed dehydration, is described.

Keywords:

• Tropane analogs
• Aldol condensation
• CNS agents
• THF

Acknowledgments

This research was supported by National Institute of Health grants DA13519 and DA00399. High resolution mass spectral determinations were carried out at the University of Kentucky Mass Spectrometry Facility.