The title tetraamino derivative was prepared by two related methods. Conversion of cis-butenediol (I) into the diamine (II) was effected by Mitsunobu condensation of (I) with HN3 with concomitant reduction of the azido group in the presence of PPh3. Acylation of (II) with mesitylenesulfonyl chloride (III) provided the bis-sulfonamide (IV), which was subsequently alkylated with the bromosulfonamide (V) in the presence of NaH to furnish the protected tetraamine (VI). The sulfonamido groups of (VI) were finally hydrolyzed by an HOAc solution of HBr in the presence of phenol.
Alternatively, diol (I) was converted to the bis-sulfonate ester (VII) under phase-transfer conditions. Alkylation of the sodium salt of N-ethyl-1,3-propanediamine disulfonamide (VIII) with the bis-mesytilate (VII) produced (VI), which was then deprotected as above.