1236157-13-3

Basic information

• Product Name: tert-butyl (R)-2-benzylazetidine-2-carboxylate
• Synonyms: tert-butyl (R)-2-benzylazetidine-2-carboxylate
• CAS NO: 1236157-13-3
• Molecular Weight: 247.337
• Mol File: 1236157-13-3.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: tert-butyl (R)-2-benzylazetidine-2-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl (R)-2-benzylazetidine-2-carboxylate(1236157-13-3)
• EPA Substance Registry System: tert-butyl (R)-2-benzylazetidine-2-carboxylate(1236157-13-3)

Safety Data

• Hazardous Substances Data: 1236157-13-3(Hazardous Substances Data)

Upstream product

• 77629-96-0 2,4-dibromobutyric acid tert-butyl ester 
• 100-39-0 benzyl bromide 
• 106-93-4 ethylene dibromide 
• 624-70-4 1-chloro-2-iodoethane 

Relevant articles and documents

Base-promoted diastereoselective α-alkylation of borane: N -((S)-1′-phenylethyl)azetidine-2-carboxylic acid ester complexes

The base-promoted α-alkylation of N-((S)-1-phenylethyl)azetidine-2-carboxylic acid esters 1 was investigated. The use of diastereomerically pure borane complexes 3 as substrates, which are easily prepared from 1, dramatically improved the yields and diastereoselectivities of α-alkylated products 2. For example, the treatment of tert-butyl ester (1S,2S,1′S)-3a with 2.4 equivalents of lithium bis(trimethysilyl)amide (LiHMDS) at 0 °C followed by 2.6 equivalents of benzyl bromide afforded α-benzylated (2S,1′S)-2aa in 90% yield as almost a single diastereomer. Our method enables the production of optically active α-substituted azetidine-2-carboxylic acid esters starting from commercially available (S)-1-phenylethylamine, which is one of the least expensive chiral compounds.