| 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
|
|
| Full text (Publisher's DOI) |
|
|
| |
|