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Title
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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. |
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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
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Publication
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Place of publication unknown
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2010
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ISSN
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1551-7004
[print]
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DOI
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10.3998/ARK.5550190.0011.309
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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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Full text (Publisher's DOI)
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