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Start Over Author "Mamolo, MARIA GRAZIA" Publisher wiley
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10. Enantioselective chromatography and absolute configuration of N,N-dimethyl-3-(naphthalen-2-yl)-butan-1-amines: potential sigma1 ligands.

Author

Collina S, Loddo G, Urbano M, Rossi D, Mamolo MG, Zampieri D, Alcaro S, Gallelli A, and Azzolina O

Subjects
Amines analysis, Amines chemistry, Amylose analogs & derivatives, Amylose chemistry, Cellulose analogs & derivatives, Cellulose chemistry, Circular Dichroism, Ligands, Models, Molecular, Molecular Structure, Naphthalenes analysis, Naphthalenes chemistry, Phenylcarbamates chemistry, Stereoisomerism, Chromatography, High Pressure Liquid methods
Abstract

We describe the preparation of racemic N,N-dimethyl-3-(naphthalen-2-yl)-butan-1-amines, potential sigma1 ligands, and their resolution via chiral HPLC. In order to obtain enantiopure compounds, direct chromatographic methods of separation using chiral stationary phases were investigated. Different methods suitable for both analytical and semipreparative purposes are proposed. The best resolutions were achieved using cellulose tris (3,5-dimethylphenyl carbamate) (Chiralcel OD and OD-H) and amylose tris (3,5-dimethylphenyl carbamate) (Chiralpak AD). On the basis of the preliminary chromatographic results, the resolution of compound 1 was transferred onto a Chiralcel OD semipreparative column. The enantiomers were obtained in high enantiomeric excess. The configurational assignment was performed by circular dichroism. Computational analysis was used to explore the enantioselective recognition process of compound 1 with the Chiralcel OD stationary phase., (2006 Wiley-Liss, Inc.)

Published
2006
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