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 = methyl-carboxyl-ate, a = acet-yloxy and me = methyl-ene]. While the N-bound ethyl-carboxyl-ate group occupies an equatorial position, the remaining substituents occupy axial positions. In the crystal, supra-molecular double-layers are formed by weak methyl- and methyl-ene-C-H⋯O(carbon-yl) inter-actions involving all four carbonyl-O atoms. The two-dimensional arrays stack along the c axis without directional inter-actions 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 inter-action energy calculations point to the importance of the dispersion energy term in the stabilization of the crystal.
Highlights
Sofia Dallasta Pedroso,a Ignez Caracelli,b* Julio Zukerman-Schpector,a Monica Soto-Monsalve,c Regina H
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]
Supramolecular double-layers are formed by weak methyl- and methylene-C—HÁ Á ÁO(carbonyl) interactions involving all four carbonyl-O atoms
Summary
A number of diseases, especially diabetes and including viral diseases, cystic fibrosis and cancer, can be treated with glucosidase inhibitors (Dhameja & Gupta, 2019; Kiappes et al, 2018); for a review of the relevant patent literature, see Bras et al (2014). The HCl salt of (I) can be prepared from (II) after being subjected to a sequence of reactions comprising a reduction step, reflux acid hydrolysis, chromatographic purification on ion-exchange resin Dowex-H+ and, hydrochloride formation In this way, (I)ÁHCl was obtained in 67% yield (Garcia, 2008). In connection with supporting structural studies (Zukerman-Schpector et al, 2017) of crucial intermediates related to the synthesis of pharmacologically active (I), the crystal and molecular structures of (II) are described. Symmetry codes: (i) Àx; Ày; Àz þ 2; (ii) x À 1; y; z; (iii) x; y À 1; z
Sign-in/Register to view highlights & summary Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callMore From: Acta crystallographica. Section E, Crystallographic communications
Disclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
