AI Article Synopsis
- The study focuses on synthesizing racemic N,N-dimethyl-3-(naphthalen-2-yl)-butan-1-amines, which could act as sigma1 receptor ligands, and explores methods for resolving these into pure enantiomers using chiral HPLC.
- Various chromatographic techniques were tested with chiral stationary phases, notably cellulose and amylose derivatives, to achieve optimal separation for both analytical and preparative goals.
- Successful resolution of the compound was achieved with the Chiralcel OD column, resulting in high enantiomeric excess, while circular dichroism was used to determine the configurations of the enantiomers, supplemented by computational analysis of the separation process.
Article 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.
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| http://dx.doi.org/10.1002/chir.20227 | DOI Listing |
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