182057-89-2

Basic information

• Product Name: 1-(2-Azido-benzoyl)-3-(tert-butyl-dimethyl-silanyloxy)-pyrrolidin-2-one
• Synonyms: 1-(2-Azido-benzoyl)-3-(tert-butyl-dimethyl-silanyloxy)-pyrrolidin-2-one
• CAS NO: 182057-89-2
• Molecular Weight: 360.488
• Mol File: 182057-89-2.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 1-(2-Azido-benzoyl)-3-(tert-butyl-dimethyl-silanyloxy)-pyrrolidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2-Azido-benzoyl)-3-(tert-butyl-dimethyl-silanyloxy)-pyrrolidin-2-one(182057-89-2)
• EPA Substance Registry System: 1-(2-Azido-benzoyl)-3-(tert-butyl-dimethyl-silanyloxy)-pyrrolidin-2-one(182057-89-2)

Safety Data

• Hazardous Substances Data: 182057-89-2(Hazardous Substances Data)

Upstream product

• 31162-13-7 2-azidobenzoic acid 
• 34897-85-3 o-azidobenzoyl chloride 
• 126645-95-2 3-<(tert-butyldimethylsilyl)oxy>-2-pyrrolidinone 

Relevant articles and documents

Synthesis of optically active vasicinone based on intramolecular aza-Wittig reaction and asymmetric oxidation

Both optical isomers of a quinazoline alkaloid, vasicinone, were synthesized by two different methods. The first method used (3S)-3-hydroxy-γ-lactam as a chiral synthon, which was, after O-TBDMS protection, o-azidobenzoylated followed by treatment with tri-n-butylphosphine to afford (S)-(-)-vasicinone via the tandem Staudinger/intramolecular aza-Wittig reaction. The second method utilized asymmetric oxygenation of deoxyvasicinone with (1S)-(+)- or (1R)-(-)-(10-camphorsulfonyl)oxaziridine (the Davis reagent), respectively. The aza-enolate anion of deoxyvasicinone was treated with (S)-(+)-reagent to afford (R)-(+)-vasicinone in 71% ee, while the reaction with (R)-(-)-reagent gave (S)-(-)-vasicinone in 62% ee. The optical purity was analyzed by HPLC on specially modified cellulose as a stationary phase. These results provided a facile method to prepare both optical isomers of vasicinone and confirmed the recently reversed stereochemistry of natural (-)-vasicinone.