Patent ID: 6121306
Filing Date: 2000-09-19
Classification: A61P,C07D

Abstract:
A process for the resolution of one desired (1R,4S) or (1S,4R) isomer of (.+-.)-1-azabicyclo[2.2.1]heptan-3-one, said process comprising:a) dissolving a mixture of (1R,4S)- and (1S,4R)-1-azabicyclo[2.2.1]heptan-3-one in a selective crystallization-effective solvent comprising one or more protic and/or aprotic solvents to form a separable mixture;b) combining with said separable mixture a di-p-toluoyltartaric acid isomer such that substantially one but not both of the following pairs of compounds will be present in said separable mixture:b)I) (1S,4R)-1-azabicyclo[2.2.1]heptan-3-one and di-p-toluoyl-L-tartaric acid; orb)ii) (1R,4S)-1-azabicyclo[2.2.1]heptan-3-one and di-p-toluoyl-d-tartaric acid;c) allowing a precipitate to form and collecting said solid precipitate from the mother liquid of said separable mixture, said precipitate comprising:c)I) (1S,4R)-1-azabicyclo[2.2.1]heptan-3-one, di-p-toluoyl-L-tartaric acid hemisalt; orc)ii) (1R,4S)-1-azabicyclo[2.2.1]heptan-3-one, di-p-toluoyl-D-tartaric acid hemisalt;wherein a precipitate comprising c)I) is obtained when said separable mixture comprises b)I) andwherein a precipitate comprising c)ii) is obtained when said separable mixture comprises b)ii).