- Selectively Protected Chiral 1,2,4-Triaminobutanes and Chiral Vicinal 1,2-Diamines
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Stepwise t-butoxycarbonylation of (S)-5-aminomethyl-2-pyrrolidone to mono-, di- and triacylated compounds has been elaborated.Ring opening of (S)-5-(Boc-aminomethyl)-N1-Boc-2-pyrrolidone with LiOH afforded the Boc-protected 4,5-diaminovaleric a
- Altman, Janina,Ben-Ishai, Dov,Beck, Wolfgang
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p. 887 - 894
(2007/10/02)
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- Synthesis of chiral 1,2,4-triaminobutanes
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(S)-5-(Azidomethyl)-2-pyrrolidone, obtained by the Mitsunobu reaction, was reduced to (S)-5-(aminomethyl)-2-pyrrolidone which was hydrolysed to (S)-4,5-diaminovaleric acid. The acid, after acylation with i-butyl or with (1R, 3R, 4S)-menthyl chloroformate, underwent a Curtius reaction yielding the corresponding (S)-1,2-dialkoxycarbonyl-1,2,4-triaminobutane. Alternatively, (S)-5-(aminomethyl)-2-pyrrolidone was subjected to exhaustive t-butoxycarbonylation followed by ring-cleavage with ammonia to give (S)-N4,N5,N5-triboc-4,5-diaminovaleramide and was converted by a Hofmann rearrangement to (S)-N1,N2-di-t-butoxy carbonyl-4-methoxycarbonyl-1,2,4-triaminobutane.
- Altman,Ben-Ishai
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