Improved process for the synthesis of enantiomeric...

Details Improved process for the synthesis of enantiomeric... Improved process for the synthesis of enantiomeric...

C - Chemistry, Metallurgy

07

C

C07C 209/16 (2006.01) C07C 29/143 (2006.01) C07C 29/145 (2006.01) C07C 269/06 (2006.01) C07C 271/44 (2006.01)

Patent

CA 2600008

A process for manufacturing (R)-propynylaminoindans, and alternatively, a process for manufacturing (S)- propynylaminoindans. The chiral propynylaminoindans include alkoxy or alkylcarbamates derivatives. The process comprises transfer or pressure hydrogenation in the presence of an optically active catalyst to reduce 1-indanones. The chiral product, either (S)- or (R)- indanols undergo nucleophilic substitution to produce the named product. In an additional aspect, the invention relates to novel intermediates and compounds, namely, substituted indanones, substituted (S)- indanols and substituted (R)- indanols.

L'invention concerne un procédé de fabrication de (R)-propynylaminoindanes, et dans une variante, un procédé de fabrication de (S)- propynylaminoindanes. Les propynylaminoindanes chiraux contiennent des dérivés alcoxy ou alkylcarbamates. Ce procédé implique l'hydrogénation par transfert ou sous pression, en présence d'un catalyseur optiquement actif pour réduire les 1-indanones. Le produit chiral, soit (S)- soit (R)- indanoles, est soumis à une substitution nucléophile pour obtenir le produit désigné. Dans un autre aspect, l'invention concerne de nouveaux intermédiaires et composés, à savoir, des indanones substitués, des (S)- indanoles substitués ainsi que des (R)- indanoles substitués.

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