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

Abstract

The title pyrrolidine compound, C18H23NO7, is a tetra-substituted species in which the five-membered ring has a twisted conformation with the twist occurring in the C—C bond bearing the adjacent acetyloxy substituents; the Cm—Ca—Ca—Cp torsion angle is −40.76 (18)° [m = methylene, a = acetyloxy and p = phenyl]. The N atom, which is sp 2-hybridized [sum of bond angles = 359.4°], bears an ethylcarboxylate substitutent and is connected to a methylene-C atom on one side and a carbon atom bearing a 4-methoxyphenyl group on the other side. Minor disorder is noted in the ethylcarboxylate substituent as well as in one of the acetyloxy groups; the major components of the disorder have site occupancies of 0.729 (9) and 0.62 (3), respectively. The most notable feature of the molecular packing is the formation of helical, supramolecular chains aligned along the b-axis direction whereby the carbonyl-O atom not involved in a disordered residue accepts C—H...O interactions from methylene-H and two-C atom separated methine-H atoms to form a six-membered {...HCCCH...O} synthon.