444313-68-2

Basic information

• Product Name: 2-Oxa-5-azabicyclo[2.2.1]heptan-3-one, 5-benzoyl-, (1R,4R)-
• CAS NO: 444313-68-2
• Molecular Formula: C12H11NO3
• Molecular Weight: 217.224
• Mol File: 444313-68-2.mol

Chemical Properties

• CAS DataBase Reference: 2-Oxa-5-azabicyclo[2.2.1]heptan-3-one, 5-benzoyl-, (1R,4R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Oxa-5-azabicyclo[2.2.1]heptan-3-one, 5-benzoyl-, (1R,4R)-(444313-68-2)
• EPA Substance Registry System: 2-Oxa-5-azabicyclo[2.2.1]heptan-3-one, 5-benzoyl-, (1R,4R)-(444313-68-2)

Safety Data

• Hazardous Substances Data: 444313-68-2(Hazardous Substances Data)

Upstream product

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

Downstream Products

• 929641-28-1 C₁₄H₁₈N₂O₄ 
• 929641-29-2 C₁₉H₁₉NO₄ 
• 929641-30-5 C₂₁H₂₃NO₃S₂ 
• 929641-31-6 C₁₉H₂₁NO₃ 
• 947280-03-7 C₁₉H₂₁NO₄ 
• 947280-04-8 C₁₉H₁₉NO₃ 
• 929641-32-7 C₁₉H₁₉NO₃ 
• 929641-33-8 C₂₀H₂₃NO₃ 
• 929641-34-9 (1S,4S)-N-benzoyl-8-methoxy-1-methyl-2,3,4,5-tetrahydro-1,4-methano-3-benzazepine 
• 126551-98-2 (–)-8-O-methylaphanorphine 

Relevant articles and documents

Stereoselective synthesis of (1R,4R)-N-acyl-2-oxa-5-aza-bicyclo[2.2.1]heptan-3-ones via mesoionic compounds. An improved synthesis of cis-4-hydroxy-D-proline

We report an asymmetric synthesis of (1R,4R)-N-acyl-2-oxa-5-aza-bicyclo[2.2.1]heptan-3-ones, starting from the inexpensive and commercially available trans-4-hydroxy-L-proline and achieved by treating N-acyl-trans-4-hydroxy-L-prolines with acetic anhydride. The formation of intermediate mesoionic compounds may explain the formation of N-acyl-2-oxa-5-aza-bicyclo[2.2.1]heptan-3-ones with (R)-absolute configuration at C(4). Acidic cleavage of these lactones readily affords N-acyl-cis-4-hydroxy-D-prolines or cis-4-hydroxy-D-proline in good yields.

Formal syntheses of (-)- and (+)-aphanorphine from (2S,4R)-4-hydroxyproline

We describe the efficient formal syntheses of both natural (-)-aphanorphine and unnatural (+)-aphanorphine from the same commercially available amino acid, (2S,4R)-4-hydroxyproline. The tricyclic framework was constructed by intramolecular Friedel-Crafts

A concise formal synthesis of unnatural (+)-aphanorphine from (2S,4R)-4-hydroxyproline

(-)-Aphanorphine methyl ether was synthesized in ten steps from commercially available (2S,4R)-4-hydroxyproline, featuring the C-2 configuration inversion of an intermediate amide and intramolecular Friedel-Crafts reaction. The present work constitutes a