186096-46-8

Basic information

• Product Name: Methyl 1-(1-phenylethyl)azetidine-2-carboxylate
• Synonyms: Methyl 1-(1-phenylethyl)azetidine-2-carboxylate
• CAS NO: 186096-46-8
• Molecular Formula: C13H17NO2
• Molecular Weight: 219.27958
• EINECS: -0
• Mol File: 186096-46-8.mol
• Article Data: 9

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Methyl 1-(1-phenylethyl)azetidine-2-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 1-(1-phenylethyl)azetidine-2-carboxylate(186096-46-8)
• EPA Substance Registry System: Methyl 1-(1-phenylethyl)azetidine-2-carboxylate(186096-46-8)

Safety Data

• Hazardous Substances Data: 186096-46-8(Hazardous Substances Data)

Upstream product

• 29547-04-4 methyl 2,4-dibromobutanoate 
• 2627-86-3 (S)-1-phenyl-ethylamine 
• 3886-69-9 (R)-1-phenyl-ethyl-amine 
• 921600-20-6 dimethyl (1'S)-1-(1'-methyl)benzylazetidine-2,2-dicarboxylate 
• 921600-22-8 dimethyl (1'S)-(1'-methyl)benzylaminomalonate 
• 204274-30-6 methyl (2R,1'S)-1-(1'-methyl)benzylazetidine-2-carboxylate 

Downstream Products

• 924630-59-1 1-[1-(1-phenyl-ethyl)-azetidin-2-yl]-propan-1-one 

Relevant articles and documents

Synthesis of optically active 2-substituted azetidine-2-carbonitriles from chiral 1-arylethylamineviaα-alkylation ofN-borane complexes

The base-promoted α-alkylation ofN-((S)-1-arylethyl)azetidine-2-carbonitriles3viaformation of theirN-borane complexes4was investigated. For example, treatment of diastereomerically pure boraneN-((S)-1′-(4′′-methoxyphenyl)ethyl)azetidine-2-carbonitrile complex (1S,2S,1′S)-4bwith 1.2 equivalents of LDA at ?78 °C followed by 1.3 equivalents of benzyl bromide at ?78 °C and warming to room temperature produced α-benzylated (2S,1′S)-5bain 72% yield and (2R,1′S)-5bain 2% yield. A mechanism for this diastereoselective α-alkylation was proposed. Our method enables the production of optically active 2-substituted azetidine-2-carbonitriles, such as α-benzylated (S)-10aand (R)-10a, starting from commercially available (S)-(1-(4-methoxyphenyl)ethyl)amine.

Synthesis of spirocyclopropyl γ-lactams by tandem intramolecular azetidine ring-opening/closing cascade reaction: Synthetic and mechanistic aspects

The scope and limitations of a novel intramolecular azetidine ring-opening/closing cascade reaction affording spirocyclopropyl γ-lactams from azetidines in high regio- and stereoselectivity is reported. The key step of the process is a SN2-type ring-opening of TMSOTf-activated azetidine rings by silyl ketene acetals generated by treatment with TMSOTf and TEA. This study is a very rare example of nucleophilic ring-opening of azetidines that does not require formation of quaternary azetidinium salts by N-alkylation or the use of N-electron-withdrawing groups. Application of this process to 2-azetidinone system led to a complete change in reactivity and provide 6-aza-bicyclo[3.2.0]heptane derivatives via an unprecedented Mukaiyama aldol-like reaction involving an ester acceptor and a silyl imidate.

Preparation of enantiopure 2-acylazetidines and their reactions with chloroformates

Enantiopure 1-phenylethylazetidine-2-carboxylates and 2-acylazetidines were prepared and reacted with chloroformates to yield α-chloro-γ-amino butyric acid esters and ketones from ring opening reaction of azetidinium ion intermediate in a completely regio- and stereoselective manner.