Process for the preparation of cis(.sup. -)-3,4-...

Details Process for the preparation of cis(.sup. -)-3,4-... Process for the preparation of cis(.sup. -)-3,4-...

C - Chemistry, Metallurgy

07

D

260/360.5

C07D 311/04 (2006.01) C07D 311/22 (2006.01) C07D 311/58 (2006.01) C07D 311/68 (2006.01) C07D 491/04 (2006.01)

Patent

CA 1118431

ABSTRACT OF THE DISCLOSURE A process for the preparation of cis-(?)-3,4- dihydro-N,N,2-trimethyl-2H-1-benzopyran-3-amine(I), a known antidepressant, is disclosed. The process of the invention is a multi-step process starting with 2-methyl-2H-1-benzopyran (II), which involves the production of novel intermediates (2 alpha, 3 beta, 4 alpha)-(?)-3,4-dihydro-2-methyl-4-(methylamino)- 2H-1-benzopyran-3-ol (IV) and its hydrogen sulfate ester (V) as well as (1a alpha, 2 beta, 7b alpha)- (?)-1,1a,2,7b-tetrahydro-1,2-dimethyl[1]benzopyrano- [3,4-b]azirine (VI) and cis-(?)-3,4-dihydro-N,2- dimethyl-2H-1-benzopyran-3-amine (VII). In the final step of the process, compound VII is methylated to form compound I.

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