Metabolites of felbamate; synthesis of 2-(4-hydroxyphenyl)-1,3-propanediol dicarbamate, 2-phenyl-2-hydroxy-1,3-propanediol dicarbamate, and 2-phenyl-1,3-propanediol monocarbamate

Three major metabolites of felbamate, namely 2-(4-hydroxyphyenyl)-1, 3-propanediol dicarbamate. [4], 2-hydroxy-2-phenyl-1,3-propanediol dicarbamat [12], and 2-phenyl-1,3-propanediol monocarbamate [17] were prepared. The first metabolite, 4, was synthesised from p-methoxy-phenylacetic acid [1] via five steps involving carboxylation, reduction, phosgenation, demethylation, and carbonation. The second one, 12, was prepared from 2-phenyl-1,3-propanediol [7] by the following five steps; phosgenation, halogenation, carbonation, dehalogenation, and ammonolysis. The synthesis of the third metabolite, 17, started with 7, via the following five steps: methylation, phosgenation, carbonation, and demethylation.