Optical resolution of 1-(1-naphthyl)ethylamine by its dicarboxylic acid derivatives: Structural features of the oxalic acid derivative diastereomeric salt pair

• Published in: Chirality (New York, N.Y.) Vol. 21; no. 3; pp. 331 - 338
• Main Authors: Bereczki, Laura, Bombicz, Petra, Bálint, József, Egri, Gabriella, Schindler, József, Pokol, György, Fogassy, Elemér, Marthi, Katalin
• Format: Journal Article
• Language: English
• Published: Hoboken Wiley Subscription Services, Inc., A Wiley Company 01.03.2009
• Subjects: achiral additive; diastereomeric crystal structures; naphthylethylamine; resolution with a derivative
• ISSN: 0899-0042; 1520-636X
• DOI: 10.1002/chir.20535

Optical resolution methods were established for racemic 1‐(1‐naphthyl) ethylamine. The resolving agents were synthesized by N‐derivatizing (R)‐1‐(1‐naphthyl) ethylamine with dicarboxylic acids. Oxalic, malonic, and succinic acid derivatives were found to be suitable resolving agents. These resolutions are parallel to a series of optical resolutions of 1‐phenylethylamine which had been previously performed by our research group using similar derivative resolving agents (Balint et al., Tetrahedron: Asymmetry 2001;12:1511–1518.) The comparison of the results of the enantiomer separations is performed. The diastereomeric salts formed with (R)‐N‐[1‐(1‐naphthyl)ethyl]oxalamic acid were investigated by single crystal X‐ray diffraction. The crystal structures were compared with the previously published structures of the diastereomers of the phenyl‐substituted analogue, namely (R)‐ and (S)‐1‐phenylethylammonium (R)‐N‐(1‐phenylethyl)oxalamates (Balint et al., Tetrahedron: Asymmetry 2001;12:1511–1518.) Chirality, 2009. © 2008 Wiley‐Liss, Inc.