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

S Bhilare, J Shah, V Gaikwad, G Gupta, YS Sanghvi… - …, 2019 - thieme-connect.com
S Bhilare, J Shah, V Gaikwad, G Gupta, YS Sanghvi, BM Bhanage, AR Kapdi
Synthesis, 2019thieme-connect.com
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 …
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.
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