145549-06-0

Basic information

• Product Name: (R)-1-((S)-2-Hydroxy-1-phenyl-ethyl)-4-phenyl-pyrrolidin-2-one
• Synonyms: (R)-1-((S)-2-Hydroxy-1-phenyl-ethyl)-4-phenyl-pyrrolidin-2-one
• CAS NO: 145549-06-0
• Molecular Weight: 281.354
• Mol File: 145549-06-0.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (R)-1-((S)-2-Hydroxy-1-phenyl-ethyl)-4-phenyl-pyrrolidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-1-((S)-2-Hydroxy-1-phenyl-ethyl)-4-phenyl-pyrrolidin-2-one(145549-06-0)
• EPA Substance Registry System: (R)-1-((S)-2-Hydroxy-1-phenyl-ethyl)-4-phenyl-pyrrolidin-2-one(145549-06-0)

Safety Data

• Hazardous Substances Data: 145549-06-0(Hazardous Substances Data)

Upstream product

• 591-51-5 phenyllithium 
• 145549-01-5 (3S,6S,7R,7aR)-5-Oxo-3,7-diphenyl-hexahydro-pyrrolo[2,1-b]oxazole-6-carboxylic acid benzyl ester 
• 145548-90-9 (3S,7aR)-5-Oxo-3-phenyl-2,3,5,7a-tetrahydro-pyrrolo[2,1-b]oxazole-6-carboxylic acid benzyl ester 
• 1026169-44-7 (3S,7aR)-5-Oxo-3-phenyl-hexahydro-pyrrolo[2,1-b]oxazole-6-carboxylic acid benzyl ester 
• 122383-34-0 (3S,7aR)-5-oxo-3-phenyl-2,3,5,6,7,7a-hexahydropyrrolo<2,1-b>oxazole 
• 145549-03-7 (3S,7R,7aR)-3,7-Diphenyl-tetrahydro-pyrrolo[2,1-b]oxazol-5-one 

Downstream Products

• 71657-88-0 (4R)-4-phenyl-2-pyrrolidone 
• 128372-78-1 (+)-(R)-1-tert-Butoxycarbonyl-4-phenyl-2-pyrrolidinone 

Relevant articles and documents

The Synthesis of Aracemic 4-Substituted Pyrrolidinones and 3-Substituted Pyrrolidines. An Asymmetric Synthesis of (-)-Rolipram

Conjugate additions of RCuCNLi to the chiral α,β-unsaturated lactam 4 gives almost exclusive exo addition - a reversal in stereochemistry when cuprates were added to chiral lactam 1.The lactams 5 were transformed into 4-substituted pyrrolidinones 8 via a three-step sequence which involved decarbalkoxylation, silane reduction and metal-ammonia benzylamine cleavage.The chemical yields as well as the enantiomeric purity were very high for this process.As an example of the usefulness of this scheme, the antidepressant (-)-Rolipram was prepared in good overall yield.Furthermore, the bicyclic lactams 6 were readily transformed, using alane as the reducing agent, to 3-substituted pyrrolidines 11.Absolute configurations of 8 and 11 were confirmed by comparison with literature assignments which also gave strong support to the facial addition of the cuprates to 4.