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

JR Hanrahan, KN Mewett, M Chebib…

Index: Hanrahan, Jane R.; Mewett, Kenneth N.; Chebib, Mary; Burden, Peter M.; Johnston, Graham A.R. Journal of the Chemical Society. Perkin Transactions 1, 2001 , # 19 p. 2389 - 2392

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Citation Number: 26

Abstract

The previously reported syntheses of TPMPA require a Mannich cyclisation to give an iodotetrahydropyridinyl intermediate prior to the Heck type coupling with an alkyl methylphosphinate to form the C–P bond. 7,15 An alternative synthesis of the related compound P4MPA (4) forms the C–P bond via a base-catalysed Pudovik addition of ethyl methylphosphinate. 16 A deoxygenation step is then necessary to afford the desired phosphinic ester. Our investigation has shown that ...