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tert-Butyl 2-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate

  • CAS No. 141293-14-3

  • Cat. No. CS-0048408
  • Purity≥97%
  • MDL No.MFCD01318910

*For research and further manufacturing use only, not for direct human use.

tert-Butyl 2-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate|CS-0048408

Structure of 141293-14-3

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General Information

  • CAS No. 141293-14-3
  • Cat. No. CS-0048408
  • Purity ≥97%
  • MDL No. MFCD01318910
  • Storage -20°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₁₃NO₃
  • Molecular Weight 183.20
  • Synonym(s) tert-Butyl 2-oxo-3-pyrroline-1-carboxylate
  • SMILES CC(C)(C)OC(=O)N1CC=CC1=O

Description

tert-Butyl 2-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate features a stable enolizable carbonyl within a five-membered heterocyclic framework, enabling direct functionalization at the C2 position. The tert-butyl ester group ensures excellent solubility and stability under standard bench conditions, facilitating use in synthetic sequences requiring mild deprotection or selective transformations.

Application

tert-Butyl 2-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate serves as a stable, bench-ready building block for the synthesis of pyrrolidine and pyrrole-based scaffolds. Its enamide functionality enables facile Michael additions, cycloadditions, and reductive amination reactions, while the tert-butyl ester group offers orthogonal protection and ease of removal under mild acidic conditions. This compound functions reliably in multi-step sequences requiring functional group tolerance and predictable reactivity.

Synthesis

  • Route1

    References

    • Zhu, Chen; Wang, Rui; Falck Organic Letters, 2012 , vol. 14, # 13 p. 3494 - 3497
  • Route2

    References

    • Casiraghi, Giovanni; Rassu, Gloria; Spanu, Pietro; Pinna, Luigi Journal of Organic Chemistry, 1992 , vol. 57, # 14 p. 3760 - 3763
  • Route3
    • null|null
      109-97-7
    • In-stock
      Di-tert-butyl dicarbonate|CS-0017817
      24424-99-5
    • ~34%
    • In-stock
      tert-Butyl 2-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate|CS-0048408
      141293-14-3

    References

    • Macdonald, Simon J.F.; Inglis, Graham G.A.; Bentley, Deborah; Dowle, Michael D. Tetrahedron Letters, 2002 , vol. 43, # 29 p. 5057 - 5060

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

  • TPSA   46.61
  • LogP   1.3199
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   0

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