A convenient diastereoselective method for the preparation of methyl (2R*,3R*)-3-aryl(pyridyl)-5-oxopyrrolidine-2-carboxylates was developed on the basis of the neutralization reaction of diastereohomogeneous dimethyl (2R*,3R*)-3-aryl(pyridyl)glutamate hydrochlorides.
Similar content being viewed by others
References
Kumar, A.; Bachhawat, A. K. Cur. Sci. 2012, 102, 288.
Monga, V.; Meena, C. L.; Kaur, N.; Jain, R. Cur. Med. Chem. 2008, 15, 2718.
Kochman, K. J. Anim. Feed Sci. 2012, 21, 3.
Lun’shina, E. V.; Gan’shina, T. S.; Makarova, L. M.; Pogorelyi, V. E.; Mirzoyan, R. S. Eksperim. Klin. Farmakol. 2003, 66, 20.
(a) Oba, M.; Saegusa, T.; Nishiyama, N.; Nishiyama, K. Tetrahedron 2009, 65, 128. (b) Panday, S. K.; Prasad, J.; Dikshit, D. K. Tetrahedron: Asymmetry 2009, 20, 1581. (c) Nájera, C.; Yus, M. Tetrahedron: Asymmetry 1999, 10, 2245.
(a) Bai, Y.-J.; Cheng, M.-L.; Zheng, X.-H.; Zhang, S.-Y.; Wang, P.-A. Chem.–Asian J. 2022, 17, e202200131. (b) Ezquerra, J.; Pedregal, C.; Merino, I.; Flórez, J.; Barluenga, J.; García-Granda, S.; Llorca M.-A. J. Org. Chem. 1999, 64, 6554. (c) Kim, B.; Song, Y.; Lee, S. Y. Chem. Commun. 2021, 57, 11052.
(a) Pachaly, P. Chem. Ber. 1971, 104, 412. (b) Pachaly, P. Chem. Ber. 1971, 104, 429. (c) Pachaly, P. Arch. Pharm. 1972, 305, 176. (d) Pachaly, P.; Daskalakis, S.; Sin, K. S. Arch. Pharm. 1984, 317, 588. (e) Zymalkowski, F.; Pachaly, P. Chem. Ber. 1967, 100, 1137.
(a) Schöllkopf, U.; Pettig, D.; Busse, U.; Egert, E.; Dyrbusch, M. Synthesis 1986, 737. (b) Hartwig, W.; Born, L. J. Org. Chem. 1987, 52, 4352.
Vasil'eva, O. S.; Berestovitskaya, B. M.; Tyurenkov, I. N.; Ostroglyadov, E. S.; Perfilova, V. N.; Gorodnicheva, N. V.; Yaremchuk, A. I. Russ. Chem. Bull. 2017, 66, 1491.
Berestovitskaya, V. M.; Vasil'eva, O. S.; Ostroglyadov, E. S.; Tyurenkov, I. N.; Anan'ev, I. V.; Lyssenko, K. A.; Perfilova, V. N.; Bagmetova, V. V. Russ. Chem. Bull. 2013, 62, 2401.
APEX2 (Version 2.1), SAINTPlus Data Reduction and Correction Program (Version 7.31A); Bruker AXS, Inc.: Madison, 2006.
SADABS; Bruker AXS, Inc.: Madison, 1997.
Sheldrick, G. M. Acta Crystallogr., Sect. A: Found. Crystallogr. 2015, A71, 3.
Sheldrick, G. M. Acta Crystallogr., Sect. C: Struct. Chem. 2015, C71, 3.
Farrugia, L. J. J. Appl. Crystallogr. 2012, 45, 849.
Spek, A. L. Acta Crystallogr., Sect. A: Found. Crystallogr. 1990, A46, 34.
Macrae, C. F.; Sovago, I.; Cottrell, S. J.; Galek, P. T. A.; McCabe, P.; Pidcock, E.; Platings, M.; Shield, G. P.; Stevens, J. S.; Towler, M.; Wood, P. A. J. Appl. Crystallogr. 2020, 53, 226.
This work was supported by the Russian Ministry of Education (project FSZN-2020-0026) and the Russian Science Foundation (project 21-15-00192).
The spectral characteristics and elemental analysis data of the synthesized compounds were obtained using the equipment of the Collective Use Center ''Physicochemical methods for the study of nitro compounds, coordination compounds, biologically active substances, and nanostructured materials'' of the Interdisciplinary Resource Center for Collective Use ''Modern physicochemical methods of the formation and study of materials for the needs of industry, science, and education'' of the Herzen State Pedagogical University of Russia.
The X-ray structural study was carried out within the framework of the State Assignment to the Federal Research Center “Kazan Scientific Center of the Russian Academy of Sciences”.
The X-ray structural study was performed using the equipment of the Distributed collective spectroanalytical center for the study of the structure, composition, and properties of substances and materials of the Federal Research Center “Kazan Scientific Center of the Russian Academy of Sciences”.
Author information
Authors and Affiliations
Corresponding author
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2023, 59(1/2), 48–53
Supplementary Information
Below is the link to the electronic supplementary material.
Rights and permissions
Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.
About this article
Cite this article
Gorodnicheva, N.V., Vasil’eva, O.S., Ostroglyadov, E.S. et al. Methyl 3-aryl(pyridyl)-5-oxopyrrolidine-2-carboxylates: synthesis and structure. Chem Heterocycl Comp 59, 48–53 (2023). https://doi.org/10.1007/s10593-023-03161-7
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10593-023-03161-7