An efficient route to all stereoisomeric enantiopure 6-amino-3-alkyl-3- azabicyclo[3.2.1]octane-6-carboxylic acids

J Org Chem. 2007 Dec 7;72(25):9811-4. doi: 10.1021/jo7019702. Epub 2007 Nov 8.

Abstract

A single-step synthesis on a gram scale of four pure stereoisomers of the 6-amino-3-azabicyclo[3.2.1]octane-6-carboxylic acid was carried out using (R)-1-phenylethylamine to confer chirality. The phenylethyl group, and the p-methoxy group linked to the N-atom, are easily removed by hydrogenolysis to afford the corresponding NH-3 derivatives. A series of N-3-alkyl compounds were prepared by way of a "one-pot" deprotection-alkylation procedure starting from the above key compounds. Their biological activity has been evaluated on the GABA receptor.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carboxylic Acids / chemical synthesis*
  • Carboxylic Acids / chemistry
  • Molecular Structure
  • Stereoisomerism
  • Tropanes / chemical synthesis*
  • Tropanes / chemistry

Substances

  • Carboxylic Acids
  • Tropanes