1-Ethyl 2-methyl 3,4-bis(acetyloxy)pyrrolidine-1,2-dicarboxylate: crystal structure, Hirshfeld surface analysis and computational chemistry

Abstract

The title compound, C13H19NO8, is based on a tetra-substituted pyrrolidine ring, which has a twisted conformation about the central C—C bond; the Cm—Ca—Ca—Cme torsion angle is 38.26 (15)° [m = methylcarboxylate, a = acetyloxy and me = methylene]. While the N-bound ethylcarboxylate group occupies an equatorial position, the remaining substituents occupy axial positions. In the crystal, supramolecular double-layers are formed by weak methyl- and methylene-C—H...O(carbonyl) interactions involving all four carbonyl-O atoms. The two-dimensional arrays stack along the c axis without directional interactions between them. The Hirshfeld surface is dominated by H...H (55.7%) and H...C/C...H (37.0%) contacts; H...H contacts are noted in the inter-double-layer region. The interaction energy calculations point to the importance of the dispersion energy term in the stabilization of the crystal.

4-Nitrobenzyl 3,4-bis(acetyloxy)-2-(4-methoxyphenyl)pyrrolidine-1-carboxylate: crystal structure, Hirshfeld surface analysis and computational chemistry

“…The structure of the title tetra-substituted pyrrolidine derivative, (I), was determined in connection with our on-going structural studies characterizing key synthetic intermediates in the synthesis of various -glucosidase inhibitors (Zukerman-Schpector et al, 2017;Dallasta Pedroso et al, 2020). -Glucosidase inhibitors are an important class of drugs employed in the treatment of a variety of diseases such as cancer, cystic fibrosis, diabetes and influenza (Kiappes et al, 2018;Dhameja & Gupta, 2019).…”

Ethyl 3,4-bis(acetyloxy)-2-(4-methoxyphenyl)pyrrolidine-1-carboxylate

“…data reports in this connection that the structure of the title tetra-substituted pyrrolidine derivative, (I), was determined in the context of supporting studies designed to provide conformational details of the molecular structures of crucial synthetic intermediates in the generation of various -glucosidase inhibitors (Zukerman-Schpector et al, 2017;Dallasta Pedroso et al, 2020a;Dallasta Pedroso et al, 2020b).…”

“…The substitution pattern in pyrrolidine (I) is comparatively rare with the most closely related structures being only recently reported. In one derivative, the difference arises as the N1-bound substituent is a 4-nitrophenylmethyl group while the other groups are the same (Dallasta Pedroso et al, 2020a) while in the other, only the substituent at the C4 differs, with the literature structure having a methylcarboxylate group (Dallasta Pedroso et al, 2020b).…”