An improved synthesis of the dopamine autoreceptor antagonist (+)-cis-8-methoxy-1-methyl-2-(dipropylamino)tetralin (AJ-76)

Abstract A new and efficient synthesis of (+)-cis-8-methoxy-1-methyl-2-(dipropylamino)tetralin, AJ-76, and its monopropyl analog, UH-232, was achieved. Relative stereochemistry was controlled by doubled bond hydrogenation, followed by enantiomeric resolution with quinine to obtain optically pure material. Overall, AJ-76 is synthesized in 9 percent overall yield, including the optical resolution.