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Ethyl 2-oxo-pyrrolidine-3-carboxylate

  • CAS No. 36821-26-8

  • Cat. No. CS-W016223
  • Molecule weight157.17
  • Purity≥95%
  • MDL No.MFCD06796534

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

Ethyl 2-oxo-pyrrolidine-3-carboxylate|CS-W016223

Structure of 36821-26-8

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General Information

  • CAS No. 36821-26-8
  • Cat. No. CS-W016223
  • Purity ≥95%
  • MDL No. MFCD06796534
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₁₁NO₃
  • Molecular Weight 157.17
  • Synonym(s) Ethyl 2-oxopyrrolidine-3-carboxylate
  • SMILES O=C(C1C(NCC1)=O)OCC

Description

Ethyl 2-oxo-pyrrolidine-3-carboxylate serves as a versatile scaffold in synthetic organic chemistry, featuring a cyclic β-keto ester moiety that enables facile functionalization. This bench-stable, moisture-tolerant reagent integrates readily into multistep syntheses, particularly for constructing nitrogen-containing heterocycles and bioactive analogs via nucleophilic additions or cycloadditions.

Application

Ethyl 2-oxo-pyrrolidine-3-carboxylate serves as a versatile building block in synthetic organic chemistry, enabling efficient access to pyrrolidine-based scaffolds. Its α,β-unsaturated carbonyl system facilitates Michael additions, nucleophilic conjugate reactions, and cyclization processes. The molecule exhibits good bench stability and is compatible with diverse functional groups, simplifying purification and integration into multi-step syntheses. It functions as a key intermediate in the construction of heterocyclic frameworks relevant to medicinal chemistry and natural product synthesis.

Synthesis

  • Route1

    References

    • CHUGAI SEIYAKU KABUSHIKI KAISHA Patent: EP1854792 A1, 2007 ; Location in patent: Page/Page column 108-109 ;
  • Route2

    References

    • Lindstrom, Kyle J.; Crooks, Stephen L. Synthetic Communications, 1990 , vol. 20, # 15 p. 2335 - 2337
  • Route3
    • Diethyl 2-(cyanomethyl)malonate|CS-0736430
      17109-93-2
    • ~%
    • In-stock
      Ethyl 2-oxo-pyrrolidine-3-carboxylate|CS-W016223
      36821-26-8

    References

    • Kato et al. Nippon Nogei Kagaku Kaishi, 1953 , vol. 27, p. 500 Chem.Abstr., 1955 , p. 3006

Safety Information

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

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Computational Chemistry Data

  • TPSA   55.4
  • LogP   -0.3144
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   2

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