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

doi:10.1021/jo0300385

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

Research output: Contribution to journal › Article › peer-review

9 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 language	English
Pages (from-to)	3976-3980
Number of pages	5
Journal	Journal of Organic Chemistry
Volume	68
Issue number	10
DOIs	https://doi.org/10.1021/jo0300385
State	Published - May 16 2003

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

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.",

author = "Janetka, {James W.} and Furness, {M. Scott} and Xiaoyan Zhang and Andrew Coop and Folk, {John E.} and Mattson, {Mariena V.} and Jacobson, {Arthur E.} and Rice, {Kenner C.}",

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T1 - Enantioconvergent synthesis of (-)-(2R,5S)-1-allyl-2,5-dimethylpiperazine, an intermediate to δ-opioid receptor ligands

AU - Janetka, James W.

AU - Furness, M. Scott

AU - Zhang, Xiaoyan

AU - Coop, Andrew

AU - Folk, John E.

AU - Mattson, Mariena V.

AU - Jacobson, Arthur E.

AU - Rice, Kenner C.

PY - 2003/5/16

Y1 - 2003/5/16

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=0038413943&partnerID=8YFLogxK

U2 - 10.1021/jo0300385

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VL - 68

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 10

ER -

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

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