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CS-W001157 4
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Ethyl 5-oxopyrrolidine-2-carboxylate

  • CAS No. 66183-71-9

  • Cat. No. CS-0148328
  • Purity≥97%
  • MDL No.MFCD00062673

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

Ethyl 5-oxopyrrolidine-2-carboxylate|CS-0148328

Structure of 66183-71-9

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General Information

  • CAS No. 66183-71-9
  • Cat. No. CS-0148328
  • Purity ≥97%
  • MDL No. MFCD00062673
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₁₁NO₃
  • Molecular Weight 157.17
  • Synonym(s) ethyl 5-oxoprolinate
  • SMILES O=C1CCC(C(OCC)=O)N1

Description

Ethyl 5-oxopyrrolidine-2-carboxylate features a cyclic lactam core with an electrophilic carbonyl at the C5 position, enabling direct functionalization at the pyrrolidine ring. This bench-stable reagent integrates readily into multistep syntheses of nitrogen-containing heterocycles, particularly in medicinal chemistry and natural product derivatization workflows.

Application

Ethyl 5-oxopyrrolidine-2-carboxylate serves as a versatile building block in synthetic organic chemistry, enabling efficient access to pyrrolidine-based scaffolds. Its enamide functionality supports diverse transformations including nucleophilic additions, metal-catalyzed couplings, and reductive amination. The molecule exhibits excellent bench stability and facilitates straightforward purification, making it well-suited for iterative synthesis workflows in medicinal chemistry and process development.

Synthesis

  • Route1
    • null|null
      64-17-5
    • In-stock
      DL-Glutamic acid|CS-W022635
      617-65-2
    • ~%
    • null|null
      55895-85-7
    • In-stock
      Ethyl 5-oxopyrrolidine-2-carboxylate|CS-0148328
      66183-71-9

    References

    • Goldschmidt GmbH Patent: EP1566375 A1, 2005 ; Location in patent: Page/Page column 5 ;
  • Route2

    References

    • Merck and Co., Inc.; Tularik Inc. Patent: US6306891 B1, 2001 ;
  • Route3
    • null|null
      64-17-5
    • In-stock
      DL-Pyroglutamic acid|CS-W013454
      149-87-1
    • ~87%
    • In-stock
      Ethyl 5-oxopyrrolidine-2-carboxylate|CS-0148328
      66183-71-9

    References

    • Rigo; Lespagnol; Pauly Journal of Heterocyclic Chemistry, 1988 , vol. 25, # 1 p. 49 - 57

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
Precautionary Statements : P264-P270-P330

Quality Control

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Computational Chemistry Data

  • TPSA   55.4
  • LogP   -0.1719
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   2

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