138078-56-5

Basic information

• Product Name: (+)-(2R,5S,7S)-1-aza-3-oxa-2-phenyl-7-(4'-nitrophenylmethyl)bicyclo<3.3.0>octan-8-one
• Synonyms: (+)-(2R,5S,7S)-1-aza-3-oxa-2-phenyl-7-(4'-nitrophenylmethyl)bicyclo<3.3.0>octan-8-one
• CAS NO: 138078-56-5
• Molecular Weight: 338.363
• Mol File: 138078-56-5.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (+)-(2R,5S,7S)-1-aza-3-oxa-2-phenyl-7-(4'-nitrophenylmethyl)bicyclo<3.3.0>octan-8-one(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-(2R,5S,7S)-1-aza-3-oxa-2-phenyl-7-(4'-nitrophenylmethyl)bicyclo<3.3.0>octan-8-one(138078-56-5)
• EPA Substance Registry System: (+)-(2R,5S,7S)-1-aza-3-oxa-2-phenyl-7-(4'-nitrophenylmethyl)bicyclo<3.3.0>octan-8-one(138078-56-5)

Safety Data

• Hazardous Substances Data: 138078-56-5(Hazardous Substances Data)

Upstream product

• 7149-65-7 ethyl (S)-pyroglutamate 
• 98-79-3 L-Pyroglutamic acid 
• 17342-08-4 (S)-Pyroglutaminol 
• 100-52-7 benzaldehyde 
• 103201-79-2 (3R,7aS)-3-phenyl-tetrahydro-pyrrolo[1,2-c]oxazol-5-one 
• 100-11-8 1-bromomethyl-4-nitro-benzene 

Relevant articles and documents

Functionalised pyrrolidinones derived from (S)-pyroglutamic acid

The generation of the lactam enolate derived from bicyclic lactams 2a-c, prepared from (S)-pyroglutamic acid 1a, and subsequent reaction with a range of electrophiles, is reported. Exo-diastereoselectivity is generally favoured. The deprotection of some of these adducts to give functionalised hydroxymethylpyrrolidinones is readily achieved by simple hemiaminal ether cleavage under acidic conditions.

(L)-pyroglutamic acid as a chiral starting material for asymmetric synthesis

Elaboration of lactam (1), readily available from (L)-pyroglutamic acid, provides access to a range of 2,4- and 2,3,4-substituted pyrrolidinones.