148357-97-5

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 145414-31-9 (S)-5-aminomethyl-2-pyrrolidone 
• 145414-30-8 (+)-(S)-5-(azidomethyl)-2-pyrrolidone 
• 17342-08-4 (S)-Pyroglutaminol 
• 4931-66-2 methyl (S)-pyroglutamate 

Downstream Products

• 156604-31-8 (2S)-N⁴-benzyloxycarbonyl-N¹,N²-di-tert-butoxycarbonyl-1,2,4-triaminobutane 

Relevant academic research and scientific papers

Selectively Protected Chiral 1,2,4-Triaminobutanes and Chiral Vicinal 1,2-Diamines

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

Synthesis of chiral 1,2,4-triaminobutanes

(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.