Synthesis of trans-3, 4-dimethyl-4-(3-hydroxyphenyl) piperidine opioid antagonists: Application of the cis-thermal elimination of carbonates to alkaloid synthesis

…, JA Ward, P Labib, RW Tharp-Taylor…

Index: Werner, John A.; Cerbone, Louis R.; Frank, Scott A.; Ward, Jeffrey A.; Labib, Parviz; Tharp-Taylor, Roger W.; Ryan Journal of Organic Chemistry, 1996 ,  vol. 61,  # 2  p. 587 - 597

Full Text: HTML

Citation Number: 46

Abstract

Improved syntheses of two trans-3, 4-dimethyl-4-(3-hydroxyphenyl) piperidine opioid antagonists from 1, 3-dimethyl-4-piperidinone are described. The 1, 3-dimethyl-4- arylpiperidinol 23 was selectively dehydrated in a two step process to the 1, 3-dimethyl-4- aryl-1, 2, 3, 6-tetrahydropyridine 26 by the cis-thermal elimination of the corresponding alkyl carbonate derivative at 190° C. In the presence of a basic nitrogen, the success of the ...