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Preparation and structural analysis of (±)-cis-ethyl 2-sulfanylidenedecahydro-1,6-naphthyridine-6-carboxylate and (±)-trans-ethyl 2-oxooctahydro-1H-pyrrolo[3,2-c]pyridine-5-carboxylate

Schwehm, Carolin; Lewis, William; Blake, Alexander J.; Kellam, Barrie; Stocks, Michael J.


Carolin Schwehm

William Lewis

Alexander J. Blake

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Professor of Medicinal Chemistry

Professor of Medicinal Chemistryand Drug Discovery


Bicycle ring closure on a mixture of (4aS,8aR)- and (4aR,8aS)-ethyl 2-oxodecahydro-1,6-naphthyridine-6-carboxylate, followed by conversion of the separated cis and trans isomers to the corresponding thioamide derivatives, gave (4aSR,8aRS)-ethyl 2-sulfanylidenedecahydro-1,6-naphthyridine-6-carboxylate, C11H18N2O2S. Structural analysis of this thioamide revealed a structure with two crystallographically independent conformers per asymmetric unit (Z? = 2). The reciprocal bicycle ring closure on (3aRS,7aRS)-ethyl 2-oxooctahydro-1H-pyrrolo[3,2-c]pyridine-5-carboxyl-ate, C10H16N2O3, was also accomplished in good overall yield. Here the five-membered ring is disordered over two positions, so that both enantiomers are represented in the asymmetric unit. The compounds act as key intermediates towards the synthesis of potential new polycyclic medicinal chemical structures.


Schwehm, C., Lewis, W., Blake, A. J., Kellam, B., & Stocks, M. J. (2014). Preparation and structural analysis of (±)-cis-ethyl 2-sulfanylidenedecahydro-1,6-naphthyridine-6-carboxylate and (±)-trans-ethyl 2-oxooctahydro-1H-pyrrolo[3,2-c]pyridine-5-carboxylate. Acta Crystallographica Section C: Structural Chemistry, 70(12), 1161-1168.

Journal Article Type Article
Acceptance Date Nov 5, 2014
Online Publication Date Nov 19, 2014
Publication Date Dec 1, 2014
Deposit Date Sep 28, 2017
Publicly Available Date Sep 28, 2017
Journal Acta Crystallographica Section C Structural Chemistry
Electronic ISSN 2053-2296
Publisher International Union of Crystallography
Peer Reviewed Peer Reviewed
Volume 70
Issue 12
Pages 1161-1168
Keywords X-ray crystal structure; privileged structure; bicycle formation; biologically active compounds; NMR evaluation; medicinal chemistry; GPCRs; polycyclic scaffolds
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Additional Information Publication: Acta Crystallographica Section C: Structural Chemistry; Content type: research papers; Article metrics: Available; Peer reviewed: Yes; Review process: Single blind; Received: 8 September 2014; Accepted: 5 November 2014; Published online: 19 November 2014; Supplementary materials: This article has supporting information; Copyright: © 2014 International Union of Crystallography


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