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7561654 
Journal Article 
Selective deprotection of N-Boc catalyzed by silica gel 
Zhang, MJ; Yuan, XH; Ma, L; Zhao, JY; Gao, LX 
2007 
1 
Gaodeng Xuexiao Huaxue Xuebao / Chemical Journal of Chinese Universities
ISSN: 0251-0790 
28 
12 
2330-2332 
Chinese 
As an important protective group of amines and amino acids, tert-butoxycarbonyl (Boc) group was extensively used in organic synthesis. Though many mild and selective reagents could be used, there is still a need for the development of a more simple and convenient method for deprotection. In this paper, a new method for the deprotection of N-Boc group with silica gel in refluxing toluene was reported. The reactions were mostly achieved in 5 h with high yields (75%-98%). N-Boc protected indoline and benzylamine, which are not deprotected with other mild method, could be deprotected with our method in good yields (89% and 95%, respectively). Additionally the deprotection of other carbamates such as Cbz, Fmoc and ethyl carbamate wasn't observed under same conditions. 
N-Boc deprotection; Selective deprotection; Silica gel 
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