Synthesis of enantiomerically pure amino-substituted fused...

C - Chemistry – Metallurgy – 07 – D

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C07D 217/22 (2006.01) C07D 215/06 (2006.01) C07D 215/20 (2006.01) C07D 215/38 (2006.01) C07D 215/40 (2006.01) C07D 215/42 (2006.01) C07D 215/48 (2006.01) C07D 221/04 (2006.01) C07D 241/42 (2006.01) C07D 307/79 (2006.01) C07D 491/04 (2006.01)

Patent

CA 2456614

This invention describes various processes for synthesis and resolution of racemic amino-substituted fused bicyclic ring systems. One process utilizes selective hydrogenation of an amino-substituted fused bicyclic aromatic ring system. An alternative process prepares the racemic amino-substituted fused bicyclic ring system via nitrosation. In addition, the present invention describes the enzymatic resolution of a racemic mixture to produce the (R)- and (S)- forms of amino-substituted fused bicyclic rings as well as a racemization process to recycle the unpreferred enantioner. Further provided by this invention is an asymmetric synthesis of the (R)- or (S)- enantioner of primary amino-substituted fused bicyclic ring systems.

L'invention concerne plusieurs procédés de synthèse et de résolution de systèmes de noyaux bicycliques fusionnés amino-substitués racémiques. Un procédé consiste à utiliser une hydrogénation sélective d'un système de noyaux aromatiques bicycliques fusionnés amino-substitués. Un autre procédé consiste à préparer le système de noyaux bicycliques fusionnés amino-substitués par nitrosation. Par ailleurs, la présente invention concerne la résolution enzymatique d'un mélange racémique en vue de produire les formes (R)- et (S)- de noyaux bicycliques fusionnés amino-substitués, ainsi qu'un procédé de racémisation permettant de recycler l'énantiomère non préféré. L'invention se rapporte en outre à une synthèse asymétrique de l'énantiomère (R)- ou (S)- de systèmes de noyaux bicycliques fusionnés amino-substitués.

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