Facile synthesis of glycol metabolites of phenethylamine drugs.
High yields of potential glycol metabolites of p-synephrine, epinephrine, octopamine, and normacromerine can be obtained from the readily available monosubstituted and disubstituted acetophenones. The general procedure involves alpha-bromination followed by displacement with acetate ion and reduction with lithium aluminum hydride. Yields ranged from 46 to 91%. Furthermore, the procedure minimizes some problems inherent in aromatic glycol synthesis which include dimerization and pinacol-pinacolone rearrangement.
D055598:Chemical Phenomena; D002621:Chemistry; D006018:Glycols / Q000138:chemical synthesis*; D010084:Oxidation-Reduction; D010627:Phenethylamines / Q000138:chemical synthesis* / Q000378:metabolism
D006018:Glycols; D010627:Phenethylamines