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

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.

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

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