150884-54-1

Basic information

• Product Name: Carbamic acid, 4-morpholinyl-, 1,1-dimethylethyl ester (9CI)
• Synonyms: Carbamic acid, 4-morpholinyl-, 1,1-dimethylethyl ester (9CI)
• CAS NO: 150884-54-1
• Molecular Formula: C9H18N2O3
• Molecular Weight: 202.25082
• Product Categories: N-BOC
• Mol File: 150884-54-1.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Carbamic acid, 4-morpholinyl-, 1,1-dimethylethyl ester (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Carbamic acid, 4-morpholinyl-, 1,1-dimethylethyl ester (9CI)(150884-54-1)
• EPA Substance Registry System: Carbamic acid, 4-morpholinyl-, 1,1-dimethylethyl ester (9CI)(150884-54-1)

Safety Data

• Hazardous Substances Data: 150884-54-1(Hazardous Substances Data)

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 36016-38-3 tert-Butyl N-hydroxycarbamate 
• 110-91-8 morpholine 
• 105838-14-0 tert-butyl N-tosyloxycarbamate 
• 1070-19-5 N-(tert-butyloxycarbonyl) azide 
• 219547-81-6 (1,2,2,2-tetrachloro-ethyl)-carbamic acid tert-butyl ester 
• 219547-79-2 t-butyl 2,2,2-trichloroethylidenecarbamate 
• 68014-21-1 triphenyl(t-butoxycarbonylimino)phosphorane 
• 42365-77-5 (2,2,2-Trichloro-1-hydroxy-ethyl)-carbamic acid tert-butyl ester 
• 4248-19-5 tert-butyl carbazate 
• 219547-77-0 t-butyl 3-(trichloromethyl)-1,2-oxaziridine-2-carboxylate 
• 163226-30-0 N-tert-butoxycarbonyl-3-(2,4-dichlorophenyl)oxaziridine 
• 150884-56-3 N-tert-butyloxycarbonyl-3-(4-cyanophenyl)oxaziridine 
• 150884-51-8 1,1-dimethylethyl N-[(4-cyanophenyl)methylen]carbamate 

Relevant articles and documents

N-Boc-O-tosyl hydroxylamine as a safe and efficient nitrogen source for the N-amination of aryl and alkyl amines: Electrophylic amination

β-Boc-protected aryl and alkyl hydrazines, useful intermediates for azapeptides and N-substituted pyrazoles, were synthesized by electrophylic amination methodology, using less energetic N-Boc-O-tosyl hydroxylamine as an efficient nitrogen source. Also we have demonstrated a two-step, chromatography-free synthesis of N-Boc-O-tosyl hydroxylamine. Georg Thieme Verlag Stuttgart - New York.

N-alkyloxycarbonyl-3-aryloxaziridines: Their preparation, structure, and utilization as electrophilic amination reagents

This paper reports the synthesis of a series of N-protected oxaziridines (N-Moc, Boc, Z or Fmoc) and discusses their ability to deliver their N-alkoxycarbonyl fragment to amines, enolates, sulfur, and phosphorus nucleophiles (electrophilic amination). These oxaziridines are prepared by oxidation of the corresponding imines with oxone or anhydrous MCPBA lithium salt as the source of oxygen. They transfer their N-protected fragment to primary and secondary amines to give protected hydrazines in fair to excelent yield. The nitrogen transfer to free amino acids (in form of their R4N+ salts) is particularly fast, even at low temperature, providing L (or D) N-protected α-hydrazino acids. Enolates are C-aminated to give N-protected α-amino ketones, esters, or amides in modest yield, due to a side aldol reaction of the unreacted enolate with the released benzaldehyde. With tertiary amines (Et3N), sulfides (PhSMe), and phosphines (Ph3P), amination and oxidation proceed in a parallel way; the amount of amination product increases when the temperature is lowered (kinetic control). Some of the factors that can orient the oxaziridine reactivity towards amination or oxidation of nucleophiles are considered.

Electrophilic Amination: Preparation and Use of N-Boc-3-(4-cyanophenyl)oxaziridine, a New Reagent That Transfers a N-Boc Group to N- and C-Nucleophiles

We describe the preparation of the title compound 2b via aza-Wittig reaction of N-Boc-triphenyliminophosphorane (6) with 4-cyanobenzaldehyde followed by Oxone oxidation of the resulting imine 5b.Oxaziridine 2b is a stable, crystalline solid, which transfers under mild conditions its N-Boc fragment to primary and secondary amines (to give Nβ-Boc-hydrazines) and enolates (to give N-Boc-amino drivatives).