Abstract
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.
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The authors thank Prof. Andrey A. Tolmachev for his encouragement and support and Ms. Yuliya Kuchkovska for her help with preparation of Fig. 3.
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The work was funded by Enamine Ltd.
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Melnykov, K.P., Volochnyuk, D.M., Ryabukhin, S.V. et al. A conformationally restricted GABA analogue based on octahydro-1H-cyclopenta[b]pyridine scaffold. Amino Acids 51, 255–261 (2019). https://doi.org/10.1007/s00726-018-2660-1
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DOI: https://doi.org/10.1007/s00726-018-2660-1