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Original scientific paper

https://doi.org/10.5562/cca2122

An Efficient Synthesis of Novel Adamantane β-Amino Acid: 2-(Adamant-2-yl)-3-aminopropanoic Acid

Vesna Petrović Peroković ; Department of Chemistry, Faculty of Science, University of Zagreb, Horvatovac 102a, 10000 Zagreb, Croatia
Rosana Ribić orcid id orcid.org/0000-0001-7611-538X ; Department of Chemistry, Faculty of Science, University of Zagreb, Horvatovac 102a, 10000 Zagreb, Croatia
Biserka Prugovečki ; Department of Chemistry, Faculty of Science, University of Zagreb, Horvatovac 102a, 10000 Zagreb, Croatia
Dubravka Matković-Čalogović ; Department of Chemistry, Faculty of Science, University of Zagreb, Horvatovac 102a, 10000 Zagreb, Croatia
Srđanka Tomić ; Department of Chemistry, Faculty of Science, University of Zagreb, Horvatovac 102a, 10000 Zagreb, Croatia


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Abstract

Novel adamantane-containing β-amino acid, 2-(adamant-2-yl)-3-aminopropanoic acid,
interesting from the aspect of medicinal chemistry, was prepared and characterized. It was synthesized in a sequence of three steps with very good overall yield. In the first step ethyl adamant-2-ylidenecyanoacetate was prepared and its crystal structure was determined. Reduction of this unsaturated cyanoacetate by catalytic hydrogenation gave the ethyl ester of the desired amino acid. 2-(Adamant-2-yl)-3-aminopropanoic acid was obtained following ester hydrolysis. (doi: 10.5562/cca2122)

Keywords

adamantane, β-amino acid synthesis, nitrile reduction, crystal structure

Hrčak ID:

93729

URI

https://hrcak.srce.hr/93729

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