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

Abstract

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(NH4)2(NO3)6 in acetonitrile at reflux. Application of the solid-supported reagent involving the use of 0.20 equiv of Ce(NH4)2(NO3)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.