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A conformationally restricted GABA analogue based on octahydro-1H-cyclopenta[b]pyridine scaffold

Amino Acids 2019, 51 (2), 255-261

DOI: 10.1007/s00726-018-2660-1

Melnykov K.; Volochnyuk D.; Ryabukhin S.; Rusanov, E.; Grygorenko O.

An approach to rel-(4aS,6R,7aR)-octahydro-1H-cyclopenta[b]pyridine-6-carboxylic acid-a bicyclic conformationally restricted gamma-aminobutyric acid (GABA) analogue was developed. The eight-step sequence relied on the reaction of 2,3-bis(chloromethyl)pyridine and a C1-binucleophile and the catalytic reduction of the pyridine ring as the key steps and allowed for the preparation of the title compound in 9.0% overall yield. Assessment of the octahydro-1H-cyclopenta[b]pyridine scaffold geometry showed that this template can be considered truly three-dimensional.

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