Resolution of Synthetic (+)- and (-)-Epibatidine by Chiral High Performance Liquid Chromatography and Identification of the Natural Enantiomer

Author:

Watt A. P.1,Verrier H. M.1,O'Connor D.1

Affiliation:

1. a Department of Medicinal Chemistry , Merck Sharp and Dohme Research Laboratories, Neuroscience Research Centre , Terlings Park, Eastwick Road, Harlow , Essex , CM20 2QR

Publisher

Informa UK Limited

Subject

Molecular Medicine

Reference7 articles.

1. Epibatidine: a novel (chloropyridyl)azabicycloheptane with potent analgesic activity from an Ecuadoran poison frog

2. Total synthesis of epibatidine

3. The synthesis of (+)- and (–)-epibatidine

4. (+)-Epibatidine. HCl, [α]D24+34.7° (c=0 36, MeOH); tr= 8.34 mins on Chiral- AGP system; tr= 12.20 mins as N-acetyl derivative on Chiralcel OD system.

5. (-)-Epibatidine HC1, [α]D24−33.7° (c=0 16. MeOH); tr= 6.68 mins on Chiral- AGP system; tr= 10.42 mins as N-acetyl derivative on Chiralcel OD system

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