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

作者：Perokovic Vesna Petrovic; Ribic Rosana^*; Prugovecki Biserka; Matkovic Calogovic Dubravka; Tomic Srdanka

来源：Croatica Chemica Acta, 2012, 85(4): 419-423.

DOI：10.5562/cca2122

• adamantane
• beta-amino acid synthesis
• nitrile reduction
• crystal structure

Novel adamantane-containing beta-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)

• 出版日期2012-12