Tetrahedron letters

A convenient synthesis of 3-substituted pipecolic acid methyl esters

C Subramanyam, S Chattarjee, JP Mallamo

Index: Subramanyam, Chakrapani; Chattarjee, Sankar; Mallamo, John P. Tetrahedron Letters, 1996 , vol. 37, # 4 p. 459 - 462

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Citation Number: 15

Abstract

A practical synthesis of the title compounds (3a-c, e) from commercially available 3-hydroxy- 2-pyridine carboxylic acid (4) is reported. The key step in the synthetic sequence involves a Pd-catalyzed cross coupling reaction of the triflate 6 with the appropriate alkyl or aryl derivatives to generate the substituted picolinic acid esters 7a-b, 8 and 11. Catalytic reduction of these picolinic acid esters provided the title compounds in good yields.