113283-89-9

Upstream product

• 110-72-5 N-ethylethane-1,2-diamine 
• 501-53-1 benzyl chloroformate 

Downstream Products

• 113283-95-7 N²-Boc-N¹-ethyl-N¹-Z-ethylenediamine 
• 113283-91-3 N¹,N²-dibenzyloxycarbonyl-N²-tert-butoxycarbonyl-N¹-ethyl-1,2-ethylenediamine 

Relevant academic research and scientific papers

Microwave-assisted carbamoylation of amines

The influence of microwave irradiation on the reaction of various amines with benzyl chloroformate and di-tert-butyl dicarbonate was investigated. Microwave irradiation was successfully applied to the carbamoylation of several nonfunctionalized and functionalized amines, including amino acids and nucleobases, leading to satisfactory to high product conversion within very short reaction times. Copyright Taylor & Francis Group, LLC.

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.