C - Chemistry – Metallurgy – 07 – D
Patent
C - Chemistry, Metallurgy
07
D
C07D 487/08 (2006.01)
Patent
CA 2269683
Racemic (+/-)-1-azabicyclo[2.2.1]heptan-3-one may be efficiently resolved into its (1S, 4R)- and (1R, 4S)-1-azabicyclo[2.2.1]heptan-3-one isomers by formation of di-p-toluoyl hemitartrate salts by combination with di-p-toluoyl- L-tartaric acid and di-p-toluoyl-D-tartaric acid, respectively. Selective crystallization using one of the di-p-toluoyltartaric acids in less that stoichiometric amount in a suitable solvent mixture allows isolation of the desired isomer as its respective di-p-toluoyl hemitartrate in high isomeric purity. The isolated hemitartrates are storage stable and may be used as such in the preparation of pharmaceuticals and other biologically active compounds, or may be used to provide the free base of the respective 1- azabicyclo[2.2.1]heptan-3-one isomer.
L'invention concerne (+/-)-1-azabicyclo[2.2.1]heptan-3-one racémique, pouvant être efficacement fractionné en ses isomères (1S, 4R)-1-azabicyclo[2.2.1]heptan-3-one et (1R, 4S)-1-azabicyclo[2.2.1]heptan-3-one par formation de ses sels d'hémitartrate de di-p-toluoyle par combinaison avec de l'acide di-p-toluoyl-L-tartrique et de l'acide di-p-toluoyl-D-tartrique, respectivement. Une cristallisation sélective à l'aide d'un des acides di-p-toluoyltartriques, en quantité inférieure à la quantité stoechiométrique, dans un mélange de solvants appropriés, permet d'isoler l'isomère souhaité comme son hémitartrate de di-p-toluoyle respectif avec une pureté isométrique élevée. Une fois stockés, les hémitartrates isolés restent stables. On peut les employer comme tels pour préparer des produits pharmaceutiques et d'autres composés biologiquement actifs, ou pour constituer la base libre de l'isomère 1-azabicyclo[2.2.1]heptan-3-one respectif.
Macrae & Co.
Warner-Lambert Company
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