944728-08-9

Basic information

• Product Name: TERT-BUTYL[(5-OXOPYRROLIDIN-2-YL)METHYL]CARBAMATE
• Synonyms: TERT-BUTYL[(5-OXOPYRROLIDIN-2-YL)METHYL]CARBAMATE
• CAS NO: 944728-08-9
• Molecular Formula: C10H17N2O3-
• Molecular Weight: 213.25358
• Mol File: 944728-08-9.mol

Chemical Properties

• Boiling Point: 404.5±18.0 °C(Predicted)
• Appearance: /
• Density: 1.086±0.06 g/cm3(Predicted)
• PKA: 12.22±0.46(Predicted)
• CAS DataBase Reference: TERT-BUTYL[(5-OXOPYRROLIDIN-2-YL)METHYL]CARBAMATE(CAS DataBase Reference)
• NIST Chemistry Reference: TERT-BUTYL[(5-OXOPYRROLIDIN-2-YL)METHYL]CARBAMATE(944728-08-9)
• EPA Substance Registry System: TERT-BUTYL[(5-OXOPYRROLIDIN-2-YL)METHYL]CARBAMATE(944728-08-9)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 944728-08-9(Hazardous Substances Data)

Upstream product

• 173828-76-7 (R)-5-(azidomethyl)-2-pyrrolidone 
• 64700-65-8 methyl (2R)-pyroglutamate 
• 66673-40-3 (R)-5-hydroxymethylpyrrolidin-2-one 
• 145414-30-8 (+)-(S)-5-(azidomethyl)-2-pyrrolidone 
• 24424-99-5 di-tert-butyl dicarbonate 
• 145414-31-9 (S)-5-aminomethyl-2-pyrrolidone 
• 173336-98-6 (5R)-5-(aminomethyl)pyrrolidin-2-one 
• 4931-66-2 methyl (S)-pyroglutamate 
• 17342-08-4 (S)-Pyroglutaminol 

Relevant articles and documents

Chiral non-racemic bis(vicinal 1,2-diamines): 4,5-diamino-N-(3,4-diaminobutyl)pentanamide tetrahydrochloride, N,N'-bis[3,4-bis(t-butoxycarbonylamino)butyl]urea and N,N'-bis[3,4-bis(t-butoxycarbonylamino)butyl]hexanamide

The reaction of (R) or (S)-N4,N5-bis(t-butoxycarbonyl)-4,5-diaminopentanoic acid (6) with (R) or (S)-N3,N4-bis(t-butoxycarbonyl)-3,4-diaminobutylisocyanate (8) catalyzed by 4-dimethylamino pyridine (DMAP), leads to the synthesis of (R,R), (S,S), (R,S) and (S,R) isomeric amides (11 a-d). The addition of adipic acid monomethyl ester to (R) or (S) isocyanate, followed by saponification, acidification and subsequent reaction with the second molecule of (R) or (S) isocyanate allows isolation of the (R,R), (S,S) and the meso isomers of N,N'-bis[3,4-bis(t-butoxycarbonylamino)butyl]hexanediamide (17). Removal of protecting groups with HCl/EtOH affords chiral non-racemic molecules having two free vicinal diamine units.

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.