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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


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
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