| Title |
Synthesis of 10-methyl-8,10-diazabicyclo[4.3.1]decane as a new building block for nicotinic modulators / |
| Authors |
Paliulis, Osvaldas ; Peters, Dan ; Holzer, Wolfgang ; Šačkus, Algirdas |
| DOI |
10.3998/ark.5550190.p008.202 |
| Full Text |
|
| Is Part of |
Arkivoc.. Gainesville : ARKAT USA. 2013, vol. 2013, iss. 4, p. 240-250.. ISSN 1551-7004. eISSN 1551-7012 |
| Keywords [eng] |
octanedioic acid ; meso-dimethyl 2,7-dibromooctanedioate ; azepane ; 8,10- diazabicyclo[4.3.1]decane |
| Abstract [eng] |
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-7,9- dione 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. |
| Published |
Gainesville : ARKAT USA |
| Type |
Journal article |
| Language |
English |
| Publication date |
2013 |
| CC license |
|
