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
• Article Data: 2

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

• 2627-86-3 (S)-1-phenyl-ethylamine 
• 23085-60-1 DL-2,4-dibromobutyric acid benzyl ester 
• 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.