Synthesis of (+)- and (-)-tetrabenazine from the resolution of -dihydrotetrabenazine
Boldt, K., Biggers, M. S., Phifer, S., Brine, G., & Rehder, K. (2009). Synthesis of (+)- and (-)-tetrabenazine from the resolution of -dihydrotetrabenazine. Synthetic Communications, 39(20), 3574-3585. DOI: 10.1080/00397910902788125
Tetrabenazine (1) was reduced with NaBH4 to ?-dihydrotetrabenazine (2) and then resolved with di-p-toluoyl-L-tartrate and di-p-toluoyl-D-tartrate to subsequently give (+)- and (?)-?-dihydrotetrabenazine. The enantiomers were oxidized under Swern conditions to prepare samples of (+)-tetrabenazine and (?)-tetrabenazine. The samples were optically pure by chiral HPLC analysis.