Syntheses of ^<15>N-Enriched Polyamines

概要

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A total synthesis of polyamines was developed using potassium phthalimide as a sole nitrogen source. ^<15>N-Enriched phthalimide was prepared almost quantitatively from ^<15>N-enriched ammonium sulfate by a modified method. Key compounds for the synthesis of ^<15>N-enriched spermidine and spermine were ^<15>N-enriched putrescine (I), N-(3-bromopropyl)-phthalimide (II), N-(4-bromobutyl) phthalimide (III), and benzylamine, which were easily prepared in high yields from potassium ^<15>N-enriched phthalimide. Spermidine was synthesized by two alternative methods involving an alkylation of monobenzyloxycarbonyl putrescine with II and a stepwise alkylation of benzylamine with II and III in the presence of KF-Celite. The lattter method allowed the preparation of all seven kinds of various ^<15>N-enriched spermidines with combinations of the three reagents containing ^<15>N or ^<14>N. Spermine was similarly synthesized by an alkylation of N, N'-dibenzylputrescine with II. In these methods, the alkylation using KF-Celite was extremely useful for the synthesis of spermidine and spermine. The present methods were also used to synthesize various other polyamines in high yields.
社団法人日本薬学会の論文
1984-09-25