31560-25-5

Basic information

• Product Name: 5-aza-5-benzoyl-2-oxa-3-oxo-bicyclo<2.2.1>heptane
• Synonyms: 5-aza-5-benzoyl-2-oxa-3-oxo-bicyclo<2.2.1>heptane
• CAS NO: 31560-25-5
• Molecular Weight: 217.224
• Mol File: 31560-25-5.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 5-aza-5-benzoyl-2-oxa-3-oxo-bicyclo<2.2.1>heptane(CAS DataBase Reference)
• NIST Chemistry Reference: 5-aza-5-benzoyl-2-oxa-3-oxo-bicyclo<2.2.1>heptane(31560-25-5)
• EPA Substance Registry System: 5-aza-5-benzoyl-2-oxa-3-oxo-bicyclo<2.2.1>heptane(31560-25-5)

Safety Data

• Hazardous Substances Data: 31560-25-5(Hazardous Substances Data)

Upstream product

• 98-88-4 benzoyl chloride 
• 51-35-4 4R-4-hydroxyproline 
• 31560-19-7 (2S,4R)-1-benzoyl-4-hydroxy-L-proline 

Downstream Products

• 120807-16-1 (2S,4R)-1-Benzoyl-4-chloro-pyrrolidine-2-carboxylic acid 
• 120806-99-7 (2S,4S)-1-Benzoyl-4-chloro-pyrrolidine-2-carboxylic acid 
• 120851-71-0 (2S,4S)-1-Benzoyl-4-phenyl-pyrrolidine-2-carboxylic acid 
• 120806-96-4 (2S,4S)-1-benzoyl-4-hydroxyproline methyl ester 
• 134003-83-1 tert-butyl (1R,4R)-5-benzyl-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate 
• 134003-84-2 tert-butyl (1R,4R)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate 

Relevant articles and documents

Synthesis of (1R,4R)-2,5-diazabicyclo[2.2.1]heptane derivatives by an epimerization-lactamization cascade reaction

An epimerization-lactamization cascade of functionalized (2S,4R)-4-aminoproline methyl esters is developed and applied in synthesizing (1R,4R)-2,5-diazabicyclo[2.2.1]heptane (DBH) derivatives. (2S,4R)-4-Aminoproline methyl esters are likely to undergo 2-epimerization under basic conditions, followed by an intramolecular aminolysis of the (2R)-epimer to form the bridged lactam intermediates. Key factors identified for this cascade reaction include the electron-withdrawal N-protective group in the substrates and a strong base as the promoter.