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Methyl 5-oxopyrrolidine-3-carboxylate

  • CAS No. 35309-35-4

  • Cat. No. CS-W003494
  • Purity≥95%
  • MDL No.MFCD08275678

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

Methyl 5-oxopyrrolidine-3-carboxylate|CS-W003494

Structure of 35309-35-4

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General Information

  • CAS No. 35309-35-4
  • Cat. No. CS-W003494
  • Purity ≥95%
  • MDL No. MFCD08275678
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₉NO₃
  • Molecular Weight 143.14
  • Synonym(s) Methyl-5-oxopyrrolidin-3-carboxylat
  • SMILES COC(=O)C1CNC(=O)C1

Description

Methyl 5-oxopyrrolidine-3-carboxylate is a versatile heterocyclic building block featuring a cyclic amide with a ketone at the C5 position and an ester at C3. This configuration enables direct functionalization at multiple sites, supporting efficient synthesis of pyrrolidine derivatives. The molecule exhibits enhanced stability under standard bench conditions and integrates readily into diverse reaction sequences.

Application

Methyl 5-oxopyrrolidine-3-carboxylate serves as a versatile building block in synthetic organic chemistry, enabling efficient access to pyrrolidine-based scaffolds through reductive amination and subsequent functionalization. The molecule's α,β-unsaturated lactam moiety facilitates conjugate additions and cycloaddition reactions, while the methyl ester group offers orthogonal handle for selective transformations. Bench-stable and readily purified by flash chromatography, it functions effectively in medicinal chemistry campaigns targeting bioactive heterocycles and peptide mimetics.

Synthesis

  • Route1

    References

    • Felluga, Fulvia; Pitacco, Giuliana; Prodan, Massimo; Pricl, Sabrina; Visintin, Marco; Valentin, Ennio Tetrahedron Asymmetry, 2001 , vol. 12, # 23 p. 3241 - 3249
  • Route2
    • null|null
      624-48-6
    • ~%
    • In-stock
      Methyl 5-oxopyrrolidine-3-carboxylate|CS-W003494
      35309-35-4

    References

    • Bulletin of the Chemical Society of Japan, , vol. 59, p. 2537 - 2546
  • Route3
    • null|null
      108303-96-4
    • ~%
    • In-stock
      Methyl 5-oxopyrrolidine-3-carboxylate|CS-W003494
      35309-35-4

    References

    • Bulletin of the Chemical Society of Japan, , vol. 59, p. 2537 - 2546

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-H312-H315-H319-H332-H335
Precautionary Statements : P260-P261-P264-P270-P271-P280-P301+P310-P302+P352-P304+P340-P304+P341-P305+P351+P338-P312-P330-P332+P313-P337+P313-P362+P364-P363-P403+P233-P405-P501

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Computational Chemistry Data

  • TPSA   55.4
  • LogP   -0.7045
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   1

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