The synthesis of 1-azatwistane

✍ Scribed by K. Heusler

• Book ID: 104238901
• Publisher: Elsevier Science
• Year: 1970
• Tongue: French
• Weight: 180 KB
• Volume: 11
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)87573-0

✦ Synopsis

In connection with a synthetic project we became interested in the preparation of substituted azatwistanes with a bridgehead nitrogen atom.

We decided to use as a bicyclic precursor 1) the cis octahydroisoquinoline 14 2, which was obtained in the following manner.

Cis-A

4 -tetrahydrophthalyl alcohol 1 3)4) was dehydrated in refluxing benzene with p-toluenesulfonic acid to give the ether 2 4) (80%) 5)-