Preparation of 3,4-dihydroisoquinolines from an acid and an...

Details Preparation of 3,4-dihydroisoquinolines from an acid and an... Preparation of 3,4-dihydroisoquinolines from an acid and an...

C - Chemistry, Metallurgy

07

D

C07D 217/18 (2006.01) C07C 231/02 (2006.01) C07D 217/02 (2006.01) C07C 235/34 (2006.01)

Patent

CA 2670834

The present invention is directed to processes for the synthesis of morphinans. In particular, a process for coupling a carboxylic acid compound with an amine compound to form an amide product that can then be isolated or the crude amide product can be cyclized to form a 3,4-dihydroisoquinoline. In one embodiment, the carboxylic acid contains a phenol moiety protected with a labile protecting group. The protected phenol reduces reaction times, simplifies work-up of the product, and reduces the amount of cyclizing agent, POCl3 that is necessary to form the 3,4-dihydroisoquinoline.

L'invention concerne des procédés de synthèse de morphinane. Elle concerne en particulier un procédé de couplage d'un composé d'acide carboxylique avec un composé d'amine afin de former un produit d'amide qui peut ensuite être isolé, ou le produit d'amide brut peut être cyclisé afin de former un composé de 3,4-dihydroisoquinoline. Dans une forme de réalisation, l'acide carboxylique contient une fraction phénol protégée par un groupe de protection instable. Le phénol protégé permet de réduire les temps de réaction, de simplifier le traitement final du produit et de réduire la quantité d'agent de cyclisation, POCl3, nécessaire pour former le composé de 3,4-dihydroisoquinoline.

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