249734-37-0

Basic information

• Product Name: BENZYL [1(1S),2R]-1-(1-PHENYLETHYL)AZETIDINE-2-CARBOXYLATE
• Synonyms: BENZYL [1(1S),2R]-1-(1-PHENYLETHYL)AZETIDINE-2-CARBOXYLATE;Benzyl[1(1R),2R]-1-(1-phenylethyl)azetidine-2-carboxylate
• CAS NO: 249734-37-0
• Molecular Formula: C₁₉H₂₁NO₂
• Molecular Weight: 295.38
• Mol File: 249734-37-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: BENZYL [1(1S),2R]-1-(1-PHENYLETHYL)AZETIDINE-2-CARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: BENZYL [1(1S),2R]-1-(1-PHENYLETHYL)AZETIDINE-2-CARBOXYLATE(249734-37-0)
• EPA Substance Registry System: BENZYL [1(1S),2R]-1-(1-PHENYLETHYL)AZETIDINE-2-CARBOXYLATE(249734-37-0)

Safety Data

• Hazardous Substances Data: 249734-37-0(Hazardous Substances Data)

Upstream product

• 23085-60-1 DL-2,4-dibromobutyric acid benzyl ester 
• 2627-86-3 (S)-1-phenyl-ethylamine 
• 100-51-6 benzyl alcohol 
• 6623-43-4 (S)-(-)-N-(2-hydroxyethyl)-α-methylbenzylamine 
• 869800-28-2 benzyl (S)-[(2-hydroxy-ethyl)-(1-phenyl-ethyl)-amino]ethanoate 
• 869800-29-3 benzyl (S)-[(2-chloro-ethyl)-(1-phenyl-ethyl)-amino]ethanoate 

Downstream Products

• 7729-30-8 (R)-azetidine-2-carboxylic acid 

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.

Practical asymmetric preparation of azetidine-2-carboxylic acid

Facile and straightforward syntheses of both enantiomers of azetidine-2-carboxylic acid are described. The syntheses depart from inexpensive chemicals and allow for the production, in five to six steps, of practical quantities of each enantiomer. Synthetic highlights include the construction of the azetidine ring using an intramolecular alkylation and the use of optically active α-methylbenzylamine as chiral auxiliary.