Title
Conjugate addition of 2-(bromomethyl)- and 2-(2-bromoethyl)piperidine to alkyl acrylates: application towards the synthesis of 2-(methoxycarbonyl)indolizidineConjugate addition of 2-(bromomethyl)- and 2-(2-bromoethyl)piperidine to alkyl acrylates: application towards the synthesis of 2-(methoxycarbonyl)indolizidine
Author
Faculty/Department
Faculty of Sciences. Chemistry
Research group
Organic synthesis
Publication type
article
Publication
,
Subject
Chemistry
Source (journal)
Arkivoc : online journal of organic chemistry. - , 2000, currens
Volume/pages
(2010):3, p. 93-101
ISSN
1551-7004
1424-6369
ISI
000273559700009
Carrier
E
Target language
English (eng)
Abstract
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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