23915-74-4Relevant academic research and scientific papers
Process for the preparation of cis-(±)-3,4-dihydro-N,N,2-trimethyl-2H-1-benzopyran-3-amine and intermediates produced thereby
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, (2008/06/13)
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 (2α,3β,4α)-(±)-3,4-dihydro-2-methyl-4-(methylamino)-2H-1-benzopyran-3-ol (IV) and its hydrogen sulfate ester (V) as well as (1aα,2β,7bα)-(±)-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.
