Publication
Title
Conjugate addition of 2-(bromomethyl)- and 2-(2-bromoethyl)piperidine to alkyl acrylates: application towards the synthesis of 2-(methoxycarbonyl)indolizidine
Author
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.
Language
English
Source (journal)
Arkivoc : online journal of organic chemistry. - Place of publication unknown, 2000, currens
Publication
Place of publication unknown : 2010
ISSN
1551-7004 [print]
1424-6369 [foutief]
Volume/pages
3(2010), p. 93-101
ISI
000273559700009
UAntwerpen
Faculty/Department
Research group
Publication type
Subject
External links
Web of Science
Record
Identification
Creation 28.01.2013
Last edited 09.04.2017