Improved Synthesis of Buprenorphine from Thebaine and/or Oripavine via Palladium??Catalyzed N??Demethylation/Acylation and/or Concomitant O??Demethylation

…, MA Endoma??Arias, DP Cox, T Hudlicky

Index: MacHara, Ales; Werner, Lukas; Endoma-Arias, Mary Ann; Cox, D. Phillip; Hudlicky, Tomas Advanced Synthesis and Catalysis, 2012 , vol. 354, # 4 p. 613 - 626

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Citation Number: 17

Abstract

Abstract An improved preparation of buprenorphine via palladium-catalyzed N- demethylation/acylation is reported. Three routes were investigated and compared in overall yield. The first involved N-demethylation/acylation of an advanced intermediate obtained from thebaine followed by hydrolysis of the N-acetamide and alkylation with cyclopropylmethyl bromide and/or reduction of the N-acetyl group with the Schwartz ...

~85%

~41%

1352741-86-6

[5α,7α]-17-acet...

~85%

~78%

~79%

~35%

Zinc (0)/dimethylformamide-mediated synthesis of symmetrical...

[Serieys, Audrey; Botuha, Candice; Chemla, Fabrice; Ferreira, Franck; Perez-Luna, Alejandro Tetrahedron Letters, 2008 , vol. 49, # 36 p. 5322 - 5323]