3-Ethyl-3-phenylpyrrolidin-2-one is a novel experimental anticonvulsant based on the α-substituted amide group pharmacophore. In order to understand pharmaceutically relevant properties of such compounds, we are conducting an extensive investigation of their structures in the solid state. In this presentation, we report chiral HPLC separation, crystal structures, and absolute configuration of enantiomers of 3-ethyl-3-phenylpyrrolidin-2-one determined using single crystal X-ray diffraction at 100 K. We demonstrate that the homochiral and racemic forms of this anticonvulsant have considerable differences in their supramolecular organization and in IR spectra in crystals. These structural differences can be related to the differences in melting points and solubility.

Solid-state structure and absolute configuration of enantiomers of 3-ethyl-3-phenylpyrrolidin-2-one

253rd National Meeting (2017)

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