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Synthesis of 5- and 6- chloropyridyl-substituted 2-azabicyclo[2.2.1]heptanes; novel epibatidine isomers

โœ Scribed by John R. Malpass; Caroline D. Cox

Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
226 KB
Volume
40
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

A synthetic route to the epibatidine analogue endo-5-(6-chloro-3-pyridyl)-2-azabicyclo[2.2.1]heptane and the corresponding endo-6-isomer is described, starting from a readily-available 2-azabicyclo[2.2.1]hept-5-ene derivative. Both the exo-5-and exo-6-compounds are also shown to be accessible from the same substrate using reductive Heck chemistry.

๐Ÿ“œ SIMILAR VOLUMES

Synthesis of epibatidine isomers: Reduct
Synthesis of epibatidine isomers: Reductive Heck coupling of 2-azabicyclo[2.2.1]hept-5-ene derivatives
โœ Caroline D. Cox; John R. Malpass ๐Ÿ“‚ Article ๐Ÿ“… 1999 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 806 KB

The coupling of N-protected 2-azabicyclo[2.2.1]hept-5-enes and 2-chloro-5-iodopyridine under reductive Heck conditions gives approximately equal amounts of exo-5-and exo-6-(6'-chloro-3'-pyridyl)-2-azabicyclo-[2.2. I]heptanes. The ratio varies slightly under a range of conditions but both products ar