Process for the production of benzopyran-2-ol derivatives

Details Process for the production of benzopyran-2-ol derivatives Process for the production of benzopyran-2-ol derivatives

C - Chemistry, Metallurgy

07

D

C07D 311/20 (2006.01) C07C 213/02 (2006.01) C07C 215/54 (2006.01) C07C 219/28 (2006.01) C07D 311/58 (2006.01)

Patent

CA 2651978

The invention provides a process for the production of a compound of formula (I), wherein Y is selected from CH3, CH2OH, CH2CH2OH, CH2Br and Br; comprising the steps of: (i) reacting a compound of formula (II), wherein OX is hydroxy or O- M+, in which M+ is a cation selected from Li+, Na+ and K+, and Y is as defined above; with trans-cinnamaldehyde (III), in the presence of a secondary amine compound; then (ii) treating the product of the preceding step with acid to afford the compound of formula (I). The above process may be used in the production of tolterodine and fesoterodine, which are useful in the treatment of overactive bladder.

L'invention porte sur un procédé de production d'un composé de la formule (I), dans laquelle Y est choisi entre CH3, CH2OH, CH2CH2OH, CH2Br et Br; lequel procédé consiste à: (i) mettre à réagir un composé de la formule (II), dans laquelle OX est hydroxy ou O- M+, où M+ est un cation choisi entre Li+, Na+ et K+, et Y est tel que défini ci-dessus, avec du trans-cinnamaldéhyde (III), en présence d'un composé amine secondaire; (ii) à traiter ensuite le produit de l'étape précédente avec un acide afin d'obtenir le composé de la formule (I). Le procédé précité peut être utilisé pour produire de la toltérodine et de la fésotérodine, qui sont destinées au traitement de la vessie hyperactive.

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