Enantioconvergent synthesis of (-)-(2R,5S)-1-allyl-2,5-dimethylpiperazine, an intermediate to δ-opioid receptor ligands

James W. Janetka, M. Scott Furness, Xiaoyan Zhang, Andrew Coop, John E. Folk, Mariena V. Mattson, Arthur E. Jacobson, Kenner C. Rice

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8 Scopus citations

Abstract

A convenient, high-yield enantioconvergent synthesis of (-)-1-allyl-(2S,5R)-dimethylpiperazine from trans-2,5-dimethylpiperazine has been developed. This compound is an important intermediate in the synthesis of Δ-opioid receptor ligands. The process allows for the laboratory preparation of 100 g quantities of this enantiomerically pure diamine without chromatography. The key steps in the sequence were an efficient optical resolution using relatively inexpensive resolving agents, followed by interconversion of the unwanted (+)-enantiomer into the desired (-)-enantiomer.

Original languageEnglish
Pages (from-to)3976-3980
Number of pages5
JournalJournal of Organic Chemistry
Volume68
Issue number10
StatePublished - May 16 2003
Externally publishedYes

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    Janetka, J. W., Furness, M. S., Zhang, X., Coop, A., Folk, J. E., Mattson, M. V., Jacobson, A. E., & Rice, K. C. (2003). Enantioconvergent synthesis of (-)-(2R,5S)-1-allyl-2,5-dimethylpiperazine, an intermediate to δ-opioid receptor ligands. Journal of Organic Chemistry, 68(10), 3976-3980.