1357356-08-1

Basic information

• Product Name: (2S,5S)-benzyl 2-(hydroxymethyl)-5-(3-methoxy-3-oxopropyl)pyrrolidine-1-carboxylate
• Synonyms: (2S,5S)-benzyl 2-(hydroxymethyl)-5-(3-methoxy-3-oxopropyl)pyrrolidine-1-carboxylate
• CAS NO: 1357356-08-1
• Molecular Weight: 321.373
• Mol File: 1357356-08-1.mol

Chemical Properties

• CAS DataBase Reference: (2S,5S)-benzyl 2-(hydroxymethyl)-5-(3-methoxy-3-oxopropyl)pyrrolidine-1-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,5S)-benzyl 2-(hydroxymethyl)-5-(3-methoxy-3-oxopropyl)pyrrolidine-1-carboxylate(1357356-08-1)
• EPA Substance Registry System: (2S,5S)-benzyl 2-(hydroxymethyl)-5-(3-methoxy-3-oxopropyl)pyrrolidine-1-carboxylate(1357356-08-1)

Safety Data

• Hazardous Substances Data: 1357356-08-1(Hazardous Substances Data)

Downstream Products

• 1357356-10-5 C₂₃H₃₃NO₄ 
• 1357356-12-7 C₂₄H₃₆N₂O₄ 
• 1357356-14-9 C₂₃H₃₃NO₃ 

Relevant articles and documents

One-pot reductive coupling of N-acylcarbamates with activated alkenes: Application to the asymmetric synthesis of pyrrolo[1,2-a]azepin-5-one ring system and (-)-xenovenine

The one-pot reductive coupling of N-acylcarbamates with activated alkenes is described. The method is based on partial reduction of N-acylcarbamates with DIBAL-H, followed by N-acyliminium ion formation and SmI2-mediated radical coupling with activated alkenes. Both acyclic and cyclic N-acylcarbamates can be used as stable substrates, and a range of activated alkenes serve as effective radical receptors. The reductive coupling of l-N-acylcarbamates 12/13 gave 2,5-disubstituted pyrrolidine derivatives in high trans-diastereoselectivities. The reductive coupling with penta-2,4-dienoate proceeded exclusively in a 1,6-addition fashion, producing a single non-conjugated E-isomer. On the basis of this method, a three-step construction of pyrrolo[1,2-a]azepin-5-one 16, the skeleton of many stemona alkaloids and lehmizidine alkaloids, and a seven-step synthesis of (-)-xenovenine (pyrrolizidine cis-223H, ent-6), the unnatural enantiomer of the frog/ant venom alkaloid possessing potent inhibitory activity towards nAChR channel, were achieved starting from l-12. The Royal Society of Chemistry 2012.