113283-91-3

Upstream product

• 38091-74-6 N-(benzyloxycarbonyl)benzamide 
• 100-51-6 benzyl alcohol 
• 121561-50-0 benzyl tert-butyl N-benzoyliminodicarbonate 
• 501-53-1 benzyl chloroformate 
• 67249-24-5 benzyl N-ethyl N-(2-hydroxyethyl) carbamate 
• 120542-13-4 benzyl N-[(tert-butoxy)carbonyl]carbamate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 113283-89-9 N¹-ethyl-N¹,N²-Z₂-ethylenediamine 

Downstream Products

• 113283-95-7 N²-Boc-N¹-ethyl-N¹-Z-ethylenediamine 
• 113283-93-5 N¹-tert-butoxycarbonyl-N²-ethylethane-1,2-diamine 

Relevant academic research and scientific papers

SYNTHESIS AND USE OF BENZYL TERT-BUTYL IMINODICARBONATE, A VERSATILE REAGENT FOR THE PREPARATION OF AMINES

An efficient synthesis of benzyl tert-butyl iminodicarbonate (IV), starting from benzoyl isocyanate, is reported.Reaction of the isocyanate with benzyl alcohol gave benzyl N-benzoylcarbamate (II) which on exhaustive tert-butoxycarbonylation via the non-isolated triacyl amine III, after aminolysis, provided the title compound.The sodium salt V was alkylated with various halides under Gabriel conditions to give in high yields the corresponding benzyloxycarbonyl tert-butoxycarbonyl diprotected amines.Similarly, compound IV was alkylated with alcohols under Mitsunobu conditions to give some additional amines of this type, from which the protecting groups can be removed selectively under mild conditions.

Selective Protection of Polyamines: Synthesis of Model Compounds and Spermidine Derivatives

A general procedure for the selective protection of mixed-primary-secondary (poly)amines, based on t-butoxycarbonylation of carbamate groups (exhaustive t-butoxycarbonylation) derived from the primary amino functions only, is reported.In most cases to be described, benzyl (poly)carbamates are used for this purpose.Subsequent removal of all benzyloxycarbonyl (Z) groups from the resulting intermediates by catalytic hydrogenolysis liberates the secondary amino functions, while t-butoxycarbonyl (Boc) is retained on the primary ones.Alternatively, selective removal of Z only from amino functions protected by both Z and Boc, which can be accomplished by base-catalysed methanolysis, results in protected (poly)amines with Boc and Z on their primary and secondary amino groups, respectively.The new reactions have been studied with two unsymmetrical derivatives of ethylene- and p-phenylene-diamine as model substances.The yields of most intermediates and the products were high.Additional experiments have been performed with spermidine to give N1,N8-Boc2-spermidine.Finally, by virtue of the non-equivalence of the two primary amino groups in this molecule, the synthesis of N8-Boc-N1-Z-spermidine by the same approach is presented.

Selective Protection of Mixed Primary-Secondary Amines. Simple Preparation of N1,N8-Bis(t-butoxycarbonyl)spermidine

A new, simple, and efficient preparative procedure of a potentially wide scope for the selective protection of mixed primary-secondary amines, based on acylation followed by exhaustive t-butoxycarbonylation is presented.