Syntheses of [13C,15N]-Labeled Polyamines

Article abstract of DOI:10.1002/1099-1344(200009)43:10<1005::AID-JLCR386>3.0.CO;2-L

[1,4-13C2, 1,4-15N2]butanediamine (1), a key compound in the syntheses of [5,8-13C2, 1,4,8-15N3]spermidine (2) and [5,8-13C2, 1,4,8,12-15N4]spermine (3), has been prepared as part of a 6-step process from 1,2-dibromoethane using potassium [13C]cyanide and potassium [15N]phthalimide. In the course of the syntheses, it was found that 1,4-dibromobutane was generated from tetrahydrofuran when bromination using triphenylphosphine and tetrabromomethane took place. A high-yield preparation of monobenzyloxycarbonyl (Z) derivative of 1, a precursor for 2, was obtained using a water-soluble Z reagent, Z-DSP, in a two-phase system of alkaline solution and chloroform. All the steps for 1, 2, and 3, were aimed at minimizing the loss of stable isotopes.