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Optical Resolution of 1-(1-naphthyl)ethylamine by Its Dicarboxylic Acid Derivatives: Structural Features of the Oxalic Acid Derivative Diastereomeric Salt Pair

Optical Resolution of 1-(1-naphthyl)ethylamine by Its Dicarboxylic Acid Derivatives: Structural Features of the Oxalic Acid Derivative Diastereomeric Salt Pair

Laura Bereczki, Petra Bombicz, József Bálint, Gabriella Egri, József Schindler, György Pokol, Elemér Fogassy, Katalin Marthi

Chirality. 2009 Mar;21(3):331-8.

PMID: 18571802

Abstract:

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).

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP10420890	(S)-(−)-1-(1-Naphthyl)ethylamine		10420-89-0	Price

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