Synthesis of selenium analogues of 1-azabicyclo[4.4.0]decane
An approach to the synthesis of selenium bicyclic structures of the 1-azabicyclo[4.4.0]decane series was developed, which included the condensation of aryl isoselenocyanates with 2-(2-bromoethyl)piperidine and subsequent intramolecular cyclization of sele
Serkov,Proshin
p. 298 - 300
(2016/11/06)
Conjugate addition of 2-(bromomethyl)- and 2-(2-bromoethyl)-piperidine to alkyl acrylates: Application towards the synthesis of 2-(methoxycarbonyl) indolizidine
Conjugate addition of 2-(bromomethyl)- and 2-(2-bromoethyl)piperidine hydrobromide to methyl and ethyl acrylate in the presence of triethylamine afforded the corresponding 3-[2-(bromomethyl)piperidin-1-yl]propanoates and 3-[2-(2-bromoethyl)piperidin-1-yl]propanoates for the first time. Furthermore, methyl 3-[2-(bromomethyl)piperidin-1-yl]propanoate was converted into the novel 2-(methoxycarbonyl)indolizidine upon treatment with lithium diisopropylamide in THF. The latter ester was easily reduced by means of lithium aluminium hydride in diethyl ether, affording 2-(hydroxymethyl)indolizidine in high yield.
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