A Convenient Synthesis of Vicinal Diamines

Article abstract of DOI:10.1021/jo00269a036

Various 3-substituted-1,2-diaminopropane compounds in which the amino groups are protected as bis(carbamates) or bis(sulfonamides) were prepared from the corresponding N,N'-bis-protected 2-(aminomethyl)aziridine derivatives by nucleophilic opening of the aziridine ring.The aziridine derivatives are ultimately derived from readily available 2-hydroxy-1,3-diaminopropane.A variety of nucleophiles can be added to incorporate various functionality (CN, O2CCH3, OH, Cl, CH3, CH2CO2H) in the 3-position of the resulting 1,2-diaminopropane derivatives.