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Conjugate addition of 2-(bromomethyl)- and 2-(2-bromoethyl)piperidine to alkyl acrylates: application towards the synthesis of 2-(methoxycarbonyl)indolizidine
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| Author |
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| Abstract |
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| 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 |
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English
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| Source (journal) |
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Arkivoc : online journal of organic chemistry. - Place of publication unknown, 2000, currens | |
| Publication |
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Place of publication unknown : 2010
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| ISSN |
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1551-7004 [print]
1424-6369 [foutief]
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| Volume/pages |
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3(2010), p. 93-101
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| ISI |
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000273559700009
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