Location of Repository

Synthesis of 10-methyl-8,10-diazabicyclo[4.3.1]decane as a new building block for nicotinic modulators

By Osvaldas Paliulis, A Dan Peters, B Wolfgang Holzer C and Algirdas Šačkus A

Abstract

A convenient method for the synthesis of 10-methyl-8,10-diazabicyclo[4.3.1]decane, possessing a novel diazabicyclic ring system, as an important synthetic organic chemistry building block was developed using octanedioic acid as a starting material. The key transformation in the 5-step synthesis sequence involved a reaction of dimethyl 2,7-dibromooctanoate with methylamine, which resulted in the formation of cis-dimethyl 1-methylazepan-2,7-dicarboxylate. The latter was further transformed into bicyclic 8-benzyl-10-methyl-8,10-diazabicyclo[4.3.1]decane-7,9dione under heating with benzylamine. Reduction of the formed bicyclic dione with lithium aluminium hydride resulted in 8-benzyl-10-methyl-8,10-diazabicyclo[4.3.1]decane, and hydrogenolysis efficiently yielded the target product

Topics: Octanedioic acid, meso-dimethyl 2, 7-dibromooctanedioate, azepane, 8, 10diazabicyclo[4.3.1]decane
Year: 2014
OAI identifier: oai:CiteSeerX.psu:10.1.1.412.2692
Provided by: CiteSeerX
Download PDF:
Sorry, we are unable to provide the full text but you may find it at the following location(s):
  • http://citeseerx.ist.psu.edu/v... (external link)
  • http://www.arkat-usa.org/get-f... (external link)
  • Suggested articles


    To submit an update or takedown request for this paper, please submit an Update/Correction/Removal Request.