Development of a novel protocol for chemoselective deprotection of N/O-benzyloxycarbonyl (Cbz) at ambient temperature
Development of a novel protocol for chemoselective deprotection of N/O-benzyloxycarbonyl (Cbz) at ambient temperature
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DOI：
10.1007/s00706-018-2276-x
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发表时间：
2018-09
期刊：
影响因子：
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通讯作者：
Mohit Saroha;K. Aggarwal;Gaurav Bartwal;J. Khurana
中科院分区：
文献类型：
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作者：
Mohit Saroha;K. Aggarwal;Gaurav Bartwal;J. Khurana
摘要 开发了一种在室温下用NaBH4和NiCl2·6H2O在甲醇中原位生成的硼化镍对N-苄氧基羰基和O-苄氧基羰基进行脱保护的新方案，得到相应的胺和酚。该方案具有化学选择性，因为氯、溴、酰胺、酯、吡啶和叔丁氧羰基部分等基团在这些条件下不受影响。脱保护也在克级反应中得到验证，以确定该协议的更广泛的适用性。图形摘要
AbstractA novel protocol for the deprotection ofN-benzyloxycarbonyl andO-benzyloxycarbonyl groups by nickel boride generated in situ from NaBH4and NiCl2·6H2O in methanol at room temperature has been developed to give the corresponding amines and phenols. This protocol is chemoselective as groups like chloro, bromo, amide, ester, pyridine, and tert-butyloxycarbonyl moiety are unaffected under these conditions. The deprotection has also been validated in gram scale reactions, to establish the wider appropriateness of this protocol.Graphical abstract