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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

(2010) ARKIVOC. p.93-101
Author
Organization
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.
Keywords
ALPHA, ENANTIOSELECTIVE SYNTHESIS, BETA-ETHYLENIC COMPOUNDS, ELECTRON-DEFICIENT ALKENES, SOLVENT-FREE CONDITIONS, BETA-AMINO ACIDS, HETEROALICYCLIC AMINOALKANOL, AZA-MICHAEL ADDITION, indolizidines, piperidines, beta-amino esters, aza-Michael reaction, ASYMMETRIC-SYNTHESIS, STEREOSELECTIVE-SYNTHESIS, CONVENIENT SYNTHESIS

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Chicago
D’hooghe, Matthias, Kourosch Abbaspour Tehrani, Christophe Buyck, and Norbert De Kimpe. 2010. “Conjugate Addition of 2-(bromomethyl)- and 2-(2-bromoethyl)piperidine to Alkyl Acrylates : Application Towards the Synthesis of 2-(methoxycarbonyl)indolizidine.” Arkivoc (3): 93–101.
APA
D’hooghe, M., Abbaspour Tehrani, K., Buyck, C., & De Kimpe, N. (2010). Conjugate addition of 2-(bromomethyl)- and 2-(2-bromoethyl)piperidine to alkyl acrylates : application towards the synthesis of 2-(methoxycarbonyl)indolizidine. ARKIVOC, (3), 93–101.
Vancouver
1.
D’hooghe M, Abbaspour Tehrani K, Buyck C, De Kimpe N. Conjugate addition of 2-(bromomethyl)- and 2-(2-bromoethyl)piperidine to alkyl acrylates : application towards the synthesis of 2-(methoxycarbonyl)indolizidine. ARKIVOC. 2010;(3):93–101.
MLA
D’hooghe, Matthias, Kourosch Abbaspour Tehrani, Christophe Buyck, et al. “Conjugate Addition of 2-(bromomethyl)- and 2-(2-bromoethyl)piperidine to Alkyl Acrylates : Application Towards the Synthesis of 2-(methoxycarbonyl)indolizidine.” ARKIVOC 3 (2010): 93–101. Print.
@article{849673,
  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.},
  author       = {D'hooghe, Matthias and Abbaspour Tehrani, Kourosch and Buyck, Christophe and De Kimpe, Norbert},
  issn         = {1551-7004},
  journal      = {ARKIVOC},
  keyword      = {ALPHA,ENANTIOSELECTIVE SYNTHESIS,BETA-ETHYLENIC COMPOUNDS,ELECTRON-DEFICIENT ALKENES,SOLVENT-FREE CONDITIONS,BETA-AMINO ACIDS,HETEROALICYCLIC AMINOALKANOL,AZA-MICHAEL ADDITION,indolizidines,piperidines,beta-amino esters,aza-Michael reaction,ASYMMETRIC-SYNTHESIS,STEREOSELECTIVE-SYNTHESIS,CONVENIENT SYNTHESIS},
  language     = {eng},
  number       = {3},
  pages        = {93--101},
  title        = {Conjugate addition of 2-(bromomethyl)- and 2-(2-bromoethyl)piperidine to alkyl acrylates : application towards the synthesis of 2-(methoxycarbonyl)indolizidine},
  url          = {http://dx.doi.org/10.3998/ark.5550190.0011.309},
  year         = {2010},
}

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