O. Paliulis, D. Peters, W. Holzer
Aug 28, 2013
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Journal
Arkivoc
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 lat ter was further transformed into bicyclic 8-benzyl-10-m ethyl-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 produ ct.