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CS-W001157 4
Total: USD 88.00

tert-Butyl 3-ethynylpyrrolidine-1-carboxylate

  • CAS No. 287193-00-4

  • Cat. No. CS-W021300
  • Purity≥97%
  • MDL No.None

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

tert-Butyl 3-ethynylpyrrolidine-1-carboxylate|CS-W021300

Structure of 287193-00-4

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General Information

  • CAS No. 287193-00-4
  • Cat. No. CS-W021300
  • Purity ≥97%
  • MDL No. None
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₁H₁₇NO₂
  • Molecular Weight 195.26
  • Synonym(s) tert-Butyl 3-ethynyl-1-pyrrolidinecarboxylate
  • SMILES CC(C)(C)OC(=O)N1CCC(C1)C#C

Description

tert-Butyl 3-ethynylpyrrolidine-1-carboxylate delivers a synthetically accessible pyrrolidine scaffold featuring a terminal alkyne handle. This bench-stable, moisture-tolerant reagent enables efficient copper-catalyzed azide-alkyne cycloaddition (CuAAC) for site-specific conjugation in drug discovery and chemical biology applications.

Application

tert-Butyl 3-ethynylpyrrolidine-1-carboxylate serves as a versatile building block in medicinal chemistry, enabling efficient access to pyrroline and pyrrolidine scaffolds via Pd-catalyzed coupling reactions. The terminal alkyne group facilitates Sonogashira, Huisgen cycloaddition, and other transition-metal-mediated transformations. Its tert-butyl carbamate protecting group offers excellent bench stability and compatibility with diverse reaction conditions, simplifying purification and enabling straightforward deprotection to the free amine.

Synthesis

  • Route1
    • Diethyl (1-diazo-2-oxopropyl)phosphonate|CS-0750348
      21047-57-4
    • In-stock
      tert-Butyl 3-formylpyrrolidine-1-carboxylate|CS-W008201
      59379-02-1
    • ~72%
    • In-stock
      tert-Butyl 3-ethynylpyrrolidine-1-carboxylate|CS-W021300
      287193-00-4

    References

    • WO2010/60952 A1, ; Page/Page column 218 ; WO 2010/060952 A1

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

Quality Control

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Computational Chemistry Data

  • TPSA   29.54
  • LogP   1.8766
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   0

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