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Ceric ammonium nitrate impregnated on silica gel in the removal of thetert-butoxycarbonyl group
Journal article

Ceric ammonium nitrate impregnated on silica gel in the removal of thetert-butoxycarbonyl group

Jih Ru Hwu, Moti L. Jain, Fu-Yuan Tsai, A. Balakumar, G.H. Hakimelahi and Shwu-Chen Tsay
Arkivoc, Vol.2002(9), pp.28-36
2002

Abstract

Amino ester Ceric ammonium nitrate Deprotection Silica gel tert-butoxycarbonyl
The tert-butoxycarbonyl group was efficiently (80-99% yields) removed from an amino, hydroxy, or mercapto functionality in organic compounds by use of 0.20 equiv of Ce(NH 4 ) 2 (NO 3 ) 6 in acetonitrile at reflux. Application of the solid-supported reagent involving the use of 0.20 equiv of Ce(NH 4 ) 2 (NO 3 ) 6 impregnated on silica gel in toluene at reflux gave the deprotected products in 90-99% yields. These reactions likely proceed through an electron transfer process.

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