Synthesis and properties of the stereoisomeric diethyl 6-aminocyclo-hexane-1,3-dicarboxylates
Abstract
Hydrogenation of diethyl 6-hydroxyiminocyclohexane-1,3-dicarboxylate (III) yielded the four stereoisomeric diethyl 6-aminocyclohexane-1,3-dicarboxylates (I), deamination of which afforded the corresponding 6-hydroxy-derivatives (II) along with cyclohexenes. The amines (I) and the alcohols (II) were characterised as their N- and O-benzoyl derivatives, respectively. Attempted preparation of the oxime (III) in acidic media yielded mainly ethyl 3,3a,4,5,6,7-hexahydro-3-oxo-2,1-benzisoxazole-5-carboxylate (IV).