Optical isomers of 2 (2 ethoxyphenoxymethyl)tetrahydro 1,4 oxazine (viloxazine) and related compounds

Article abstract of DOI:10.1021/jm00230a021

The optical isomers of 2 (2 ethoxyphenoxymethyl)tetrahydro 1,4 oxazine (viloxazine) and 2 (3 methoxyphenoxymethyl)tetrahydro 1,4 oxazine have been prepared and absolute configurations have been assigned. In their action on the central nervous system the S isomers are at least ten times more potent than the R isomers. The intermediate 4 benzyl 2 (p toluenesulfonyloxymethyl) tetrahydro 1,4 oxazine has been resolved. Its isomers provide a convenient starting point for the preparation of optical isomers of viloxazine analogues of known configuration.