77647-98-4

Basic information

• Product Name: tert-butyl N-benzylazetidine-2-carboxylate
• Synonyms: tert-butyl N-benzylazetidine-2-carboxylate
• CAS NO: 77647-98-4
• Molecular Weight: 247.337
• Mol File: 77647-98-4.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: tert-butyl N-benzylazetidine-2-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl N-benzylazetidine-2-carboxylate(77647-98-4)
• EPA Substance Registry System: tert-butyl N-benzylazetidine-2-carboxylate(77647-98-4)

Safety Data

• Hazardous Substances Data: 77647-98-4(Hazardous Substances Data)

Upstream product

• 104-63-2 N-Benzylethanolamine 
• 107-59-5 tert-Butyl chloroacetate 
• 1269460-91-4 C₁₅H₂₂ClNO₂ 
• 168263-75-0 tert-butyl 2-(benzyl-(2-hydroxyethyl)amino)-acetate 
• 77629-96-0 2,4-dibromobutyric acid tert-butyl ester 
• 100-46-9 benzylamine 

Downstream Products

• 1269461-40-6 C₁₂H₁₄N₄O₂ 
• 1269461-42-8 C₁₃H₁₄N₂O₂ 
• 31247-34-4 (1-benzyl-azetidin-2-yl)-methanol 
• 1353161-08-6 tert-butyl N-benzyl-2-(2-methoxycarbonylethyl)azetidine-2-carboxylate 
• 4458-64-4 N-benzyl-2-azetidinone 
• 70339-93-4 N-Benzyl-Δ¹-azetinium Perchlorate 

Relevant articles and documents

Structural and mechanistic studies of the base-induced Sommelet-Hauser rearrangement of: N -α-branched benzylic azetidine-2-carboxylic acid-derived ammonium salts

The base-induced Sommelet-Hauser rearrangement of N-α-branched benzylic azetidine-2-carboxylic acid ester-derived ammonium salts to obtain α-arylazetidine-2-carboxylic acid esters was investigated. The substrates, two diastereomeric salts (1S,2S,1′S)- and (1R,2R,1′S)-2, showed different reactivities. The rearrangement of (1S,2S,1′S)-2a proceeded with a perfect N-to-C chirality transfer to provide (R)-3a in 74% yield with 99% ee. However, the rearrangement of (1R,2R,1′S)-2a under the same conditions afforded (S)-3a in only 15% yield with a lower 66% ee, along with the competitive [1,2] Stevens rearrangement product 4a. Structural and mechanistic studies of this rearrangement were carried out to clarify the exact reason. Our results define the scope and limitations of the Sommelet-Hauser rearrangement and provide unique synthetic access to α-aryl amino acid derivatives.

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 β-lactams from azetidine-2-carboxylic acids and esters

-