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Synthesis 1988; 1988(12): 992-994
DOI: 10.1055/s-1988-27780
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Convenient Preparation of Alkyl Benzyl Imidodicarbonates, Useful Reagents for the Direct Synthesis of Protected Amines

Leif Grehn* , M. Lurdes, S. Almeida, Ulf Ragnarsson
  • *Department of Biochemistry, University of Uppsala, Biomedical Center, P.O. Box 576, S-75123 Uppsala, Sweden
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Publication Date:
20 August 2002 (online)

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New mixed alkyl benzyl imidodicarbonates were prepared by reaction of benzyloxycarbonyl isocyanate with appropriate alcohols. This simple procedure also furnished alternative, more convenient routes to dibenzyl and benzyl 9-fluorenylmethyl imidodicarbonates. The substances are of interest as potential Gabriel reagents. Completely selective removal of one of the alkoxycarbonyl groups from the N-atom of the imidodicarbonates was demonstrated in several instances, giving benzyl carbamate or the alternative carbamate.