459426-36-9

Basic information

• Product Name: ethyl 1-((S)-1-phenylethyl)azetidine-2-carboxylate
• Synonyms: ethyl 1-((S)-1-phenylethyl)azetidine-2-carboxylate
• CAS NO: 459426-36-9
• Molecular Weight: 233.31
• Mol File: 459426-36-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: ethyl 1-((S)-1-phenylethyl)azetidine-2-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 1-((S)-1-phenylethyl)azetidine-2-carboxylate(459426-36-9)
• EPA Substance Registry System: ethyl 1-((S)-1-phenylethyl)azetidine-2-carboxylate(459426-36-9)

Safety Data

• Hazardous Substances Data: 459426-36-9(Hazardous Substances Data)

Upstream product

• 2627-86-3 (S)-1-phenyl-ethylamine 
• 36847-51-5 ethyl 2,4-dibromobutyrate 
• 869800-24-8 [1(1S),2S]-1-(1-phenyl-ethyl)-azetidine-2-carbonitrile 
• 64-17-5 ethanol 

Downstream Products

• 1047987-42-7 C₁₂H₁₇NO 
• 1158445-88-5 C₁₇H₂₃NO₂ 
• 1158445-86-3 CF₃O₃S^(1-)*C₁₇H₂₄NO₂⁽¹⁺⁾ 

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.

Rearrangement of 2-hydroxyalkylazetidines into 3-fluoropyrrolidines

Upon treatment with DAST (diethylaminosulfur trifluoride) enantiopure 2-hydroxyalkylazetidines rearrange into 3-fluoropyrrolidines. The reaction is stereospecific and involves a bicyclic 1-azoniabicyclo[2.1.0]pentane intermediate which is regioselectively opened by a fluoride anion. Georg Thieme Verlag Stuttgart.