A conformationally restricted GABA analogue based on octahydro-1H-cyclopenta[b]pyridine scaffold
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An approach to rel-(4aS,6R,7aR)-octahydro-1H-cyclopenta[b]pyridine-6-carboxylic acid—a bicyclic conformationally restricted γ-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.
KeywordsConformational restriction Amino acids Bicyclic compounds Pyridine Hydrogenation GABA analogues
The authors thank Prof. Andrey A. Tolmachev for his encouragement and support and Ms. Yuliya Kuchkovska for her help with preparation of Fig. 3.
Compliance with ethical standards
Conflict of interest
The authors declare no conflict of interests.
The work was funded by Enamine Ltd.
This article does not contain any studies with human participants or animals performed by any of the authors.
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