SELECTIVELY PROTECTED CHIRAL 1,2,4-TRIAMINOBUTANES AND CHIRAL VICINAL1,2-DIAMINES

Stepwise t-butoxycarbonylation of (S)-5-aminomethyl-2-pyrrolidone to m ono-, di- and triacylated compounds has been elaborated. Ring opening of (S)-5-(Boc-aminomethyl)-N-1-Boc-2-pyrrolidone with LiOH afforded th e Boc-protected 4,5-diaminovaleric acid, whereas with NaBH4 the Boc-pr otected (S)4,5-diamino-pentanol was obtained The acid underwent Curtiu s rearrangement to the corresponding isocyanate which was transformed to (S)-N-1,N-2-di-Boc-1,2,4-triaminobutane and to N-1,N-2-di-Boc-N-4-Z -triaminobutane. Curtius rearrangement of (S)-N-4,N-5-di-Z-valeric aci d and pTSA catalyzed addition of t-BuOH to the isocyanate, yielded N-1 ,N-2-di-Z-N-4-Boc-1,2,4-triaminobutane.