title: Enantioselective chromatography and absolute configuration of N,N-dimethyl-3-(naphthalen-2-yl)-butan-1-amines: potential sigma1 ligands.
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.
authors.affiliation: Dipartimento di Chimica Farmaceutica, Università di Pavia, Pavia, Italy.
authors.forename: Simona
authors.initials: S
authors.lastname: Collina
authors.forename: Guya
authors.initials: G
authors.lastname: Loddo
authors.forename: Mariangela
authors.initials: M
authors.lastname: Urbano
authors.forename: Daniela
authors.initials: D
authors.lastname: Rossi
authors.forename: Maria Grazia
authors.initials: MG
authors.lastname: Mamolo
authors.forename: Daniele
authors.initials: D
authors.lastname: Zampieri
authors.forename: Stefano
authors.initials: S
authors.lastname: Alcaro
authors.forename: Andrea
authors.initials: A
authors.lastname: Gallelli
authors.forename: Ornella
authors.initials: O
authors.lastname: Azzolina
mesh_terms: D000588:Amines / Q000032:analysis / Q000737:chemistry; D000688:Amylose / Q000031:analogs & derivatives / Q000737:chemistry; D002482:Cellulose / Q000031:analogs & derivatives / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D002942:Circular Dichroism; D008024:Ligands; D008958:Models, Molecular; D015394:Molecular Structure; D009281:Naphthalenes / Q000032:analysis / Q000737:chemistry; D048448:Phenylcarbamates / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000588:Amines; D008024:Ligands; D009281:Naphthalenes; D048448:Phenylcarbamates; C065943:cellulose tris-3,5-dimethylphenyl-carbamate; C080033:Chiralpak AD; D002482:Cellulose; D000688:Amylose