Pd/PTABS: An Efficient Catalytic System for the Aminocarbonylation of a Sugar-Protected Nucleoside

Author:

Bhilare Shatrughn1,Shah Jagrut1,Gaikwad Vinayak1,Gupta Gaurav1,Sanghvi Yogesh S.2,Bhanage Bhalchandra M.1,Kapdi Anant R.1

Affiliation:

1. Department of Chemistry, Institute of Chemical Technology

2. Rasayan Inc.

Abstract

A highly efficient and mild protocol for the aminocarbonylation of a nucleoside is developed by employing palladium/(1,3,5-triaza-7-phosphaadamantan-1-ium-1-yl)butane-1-sulfonate (Pd/PTABS) as the catalytic system. The developed aminocarbonylation methodology employs CO gas at a relatively low temperature of 60 °C and is suitable for a wide range of amines, including (heteroaryl)benzylic, aliphatic acyclic, alicyclic and secondary amines. This protocol is also utilized for the synthesis of a sangivamycin precursor by carrying out the Pd-catalyzed amination and aminocarbonylation simultaneously. The utility of this protocol is further demonstrated by the synthesis of the drugs moclobemide and nikethamide.

Publisher

Georg Thieme Verlag KG

Subject

Organic Chemistry,Catalysis

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