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

Petrović Peroković, Vesna and Ribić, Rosana and Prugovečki, Biserka and Matković-Čalogović, Dubravka and Tomić, Srđanka (2012) An Efficient Synthesis of Novel Adamantane β-Amino Acid: 2-(Adamant-2-yl)-3-aminopropanoic Acid. Croatica Chemica Acta, 85 (4). pp. 419-423. ISSN 0011-1643

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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.

Item Type: Article
Keywords: adamantane; β-amino acid synthesis; nitrile reduction; crystal structure
Date: 2012
Subjects: NATURAL SCIENCES > Chemistry
Divisions: Faculty of Science > Department of Chemistry
Publisher: Hrvatsko kemijsko društvo
Related URLs:
Depositing User: Branka Maravic
Date Deposited: 28 Apr 2014 12:40
Last Modified: 28 Apr 2014 12:40
URI: http://digre.pmf.unizg.hr/id/eprint/989

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