Alternate synthesis of 1,4-diamino-cyclohexane-1,4-dicarboxylic acid dimethyl ester

CHED 289

Derek M. Dalton, dmdalton@gmail.com and Melissa Axen, melissa-axen@lycos.com. Department of Chemistry, University of Colorado Denver, 1111 W. Colfax Ave., Denver, CO 80217
The purpose of the research is to investigate an alternative route to the synthesis of 1,4-diamino-cyclohexane-1,4-dicarboxylic acid dimethyl ester for cyclization and use as an enzyme inhibitor, biodegradable polymer or cell membrane transport. The current synthetic route produces a bis-zwitterion intermediate that has limited solubility, resulting in low product yields. The alternate route avoids the bis-zwitterion intermediate by incorporating a protecting group on one side of the substrate. This allows unilateral manipulation of the substrate. The result is a zwitterion intermediate and the bis-zwitterion is avoided. Principal findings show that the mono-protected substrate is generated in 50% yield. Initial results from the Strecker synthesis and the subsequent hydrolysis of the mono-protected substrate show quantitative yields but require further analysis. The results from the principle steps of the alternate route are encouraging. The research will continue and further results will be presented.