1,2,5-Substituted derivatives of 2-phenylpyrrolidine
The structures of the potential anti-human-immunodeficiency virus type 1 (HIV-1) non-nucleoside reverse transcriptase inhibitors (NNRTI) 1-tert-butoxycarbonyl-2-phenylpyrrolidine-2-carboxylic acid, C16H21NO4, (I), and 2-ammoniomethyl-1-benzyl-5-oxo-2-phenylpyrrolidine chloride, C18H21N2O+·Cl−, (II), have been investigated by X-ray diffraction. The investigations confirm a butterfly-like conformation for both compounds. In (I), the pyrrolidine ring has a marked half-chair conformation, while it has a weakly pronounced envelope conformation in (II). Intermolecular hydrogen bonds, viz. O—H…O in (I), and N—H…O and N—H…Cl in (II), build infinite chains in both structures. Rotational disorder of the three methyl groups is observed in (I).
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Document Type: Research Article
Publication date: 2004-06-01