Deoxygenation of Phenolic Alkaloids by a Modified Pd/C-Catalyzed Hydrogenolysis Method

Chin-Ting Lin; Shoie-Sheng Lee

doi:10.1055/s-0034-1380206

Synthesis, Table of Contents

Synthesis 2015; 47(17): 2586-2592
DOI: 10.1055/s-0034-1380206

paper

Deoxygenation of Phenolic Alkaloids by a Modified Pd/C-Catalyzed Hydrogenolysis Method

Chin-Ting Lin

School of Pharmacy, College of Medicine, National Taiwan University, No. 33, Linsen S. Rd., Zhongzheng Dist., Taipei 100, Taiwan ROC Email: shoeilee@ntu.edu.tw

,

Shoie-Sheng Lee*

School of Pharmacy, College of Medicine, National Taiwan University, No. 33, Linsen S. Rd., Zhongzheng Dist., Taipei 100, Taiwan ROC Email: shoeilee@ntu.edu.tw

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Abstract

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Abstract

A modified palladium on carbon (Pd/C) catalyzed hydrogenolysis method for the removal of the phenolic-OH group in phenolic alkaloids as the 1-phenyl-1H-tetrazol-5-yl derivative by the addition of magnesium metal or ammonium acetate in acetic acid is described. Five different types of isoquinoline alkaloids, i.e., phenanthrene alkaloid, aporphine, pavine, protoberberine, and 1-benzyltetrahydroisoquinoline, were used as reactants. The results indicate that the addition of either magnesium metal or ammonium acetate has the advantage of decreasing the amount of Pd/C and the accelerating reaction rate over the simple Pd/C-catalyzed hydrogenolysis, thus it is practical for larger-scale preparation of de-phenolated alkaloids for pharmacological study.

Key words

phenolic alkaloids - de-phenolation - 1-phenyl-1H-tetrazol-5-yl ether - ammonium acetate - magnesium

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References

References

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