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Development of a novel protocol for chemoselective deprotection of N/O-benzyloxycarbonyl (Cbz) at ambient temperature

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Abstract

A novel protocol for the deprotection of N-benzyloxycarbonyl and O-benzyloxycarbonyl groups by nickel boride generated in situ from NaBH4 and 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.

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Acknowledgements

M. S. and G. B. thank CSIR, New Delhi, India for the Grant of SPM Fellowship and JRF and SRF, respectively. Authors also acknowledge University of Delhi for providing us University Grant and DST Purse Grant.

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Authors and Affiliations

  1. Department of Chemistry, University of Delhi, Delhi, 110007, India

    Mohit Saroha, Komal Aggarwal, Gaurav Bartwal & Jitender M. Khurana

Authors
  1. Mohit Saroha
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  2. Komal Aggarwal
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  3. Gaurav Bartwal
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  4. Jitender M. Khurana
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Corresponding author

Correspondence to Jitender M. Khurana.

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Saroha, M., Aggarwal, K., Bartwal, G. et al. Development of a novel protocol for chemoselective deprotection of N/O-benzyloxycarbonyl (Cbz) at ambient temperature. Monatsh Chem 149, 2231–2235 (2018). https://doi.org/10.1007/s00706-018-2276-x

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  • DOI: https://doi.org/10.1007/s00706-018-2276-x

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