An improved, versatile synthesis of the GABAC antagonists (1,2,5,6-tetrahydropyridin-4-yl)methylphosphinic acid (TPMPA) and (piperidin-4-yl)methylphosphinic acid (P4MPA)

Jane R. Hanrahan; Kenneth N. Mewett; Mary Chebib; Peter M. Burden; Graham A. R. Johnston

doi:10.1039/B105989K

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An improved, versatile synthesis of the GABA_Cantagonists(1,2,5,6-tetrahydropyridin-4-yl)methylphosphinic acid (TPMPA) and (piperidin-4-yl)methylphosphinic acid (P4MPA)

Jane R. Hanrahan,*^a Kenneth N. Mewett,^a Mary Chebib,^b Peter M. Burden^a and Graham A. R. Johnston^a

Author affiliations

* Corresponding authors

^a The Adrien Albert Laboratory of Medicinal Chemistry, Department of Pharmacology, The University of Sydney, Australia
E-mail: sacjrh@pharmacol.usyd.edu.au
Fax: 02 9351 3868
Tel: 02 93516204

^b The Faculty of Pharmacy, The University of Sydney, Australia
E-mail: maryc@pharm.usyd.edu.au
Fax: 02 9351 4391
Tel: 02 9351 8584

Abstract

A simple, versatile and economical synthesis of the highly selective GABA_C antagonist (1,2,5,6-tetrahydropyridin-4-yl)methylphosphinic acid (TPMPA) and the saturated analogue P4MPA is described. TPMPA is prepared in high yield in five steps via a palladium catalysed C–P bond forming reaction.

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Article information

DOI: https://doi.org/10.1039/B105989K
Article type: Paper
Submitted: 05 Jul 2001
Accepted: 06 Aug 2001
First published: 13 Sep 2001

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J. Chem. Soc., Perkin Trans. 1, 2001, 2389-2392

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An improved, versatile synthesis of the GABA_C antagonists (1,2,5,6-tetrahydropyridin-4-yl)methylphosphinic acid (TPMPA) and (piperidin-4-yl)methylphosphinic acid (P4MPA)

J. R. Hanrahan, K. N. Mewett, M. Chebib, P. M. Burden and G. A. R. Johnston, J. Chem. Soc., Perkin Trans. 1, 2001, 2389 DOI: 10.1039/B105989K

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Journal of the Chemical Society, Perkin Transactions 1