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CS-W001157 4
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tert-Butyl 2-cyanopyrrolidine-1-carboxylate

  • CAS No. 144688-70-0

  • Cat. No. CS-W002838
  • Purity≥98%
  • MDL No.MFCD01861225

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

tert-Butyl 2-cyanopyrrolidine-1-carboxylate|CS-W002838

Structure of 144688-70-0

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General Information

  • CAS No. 144688-70-0
  • Cat. No. CS-W002838
  • Purity ≥98%
  • MDL No. MFCD01861225
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₁₆N₂O₂
  • Molecular Weight 196.25
  • Synonym(s) None
  • SMILES N#CC1CCCN1C(=O)OC(C)(C)C

Description

tert-Butyl 2-cyanopyrrolidine-1-carboxylate features a pyrrolidine core with a strategically positioned cyano group and a robust tert-butoxycarbonyl protecting group. This combination enables stable incorporation into complex molecular architectures, facilitating efficient access to nitrogen-containing heterocycles under standard conditions.

Application

tert-Butyl 2-cyanopyrrolidine-1-carboxylate serves as a versatile building block in medicinal chemistry, enabling efficient access to pyrrolidine-based scaffolds. The nitrile group facilitates transformations such as hydrolysis, reduction, and cyclization, while the tert-butyl carbamate offers stability and orthogonal deprotection under mild acidic conditions. Its compatibility with diverse reaction conditions supports applications in API synthesis, peptide modification, and heterocycle construction.

Synthesis

  • Route1
    • null|null
      19158-51-1
    • In-stock
      tert-Butyl pyrrolidine-1-carboxylate|CS-W001661
      86953-79-9
    • ~95%
    • In-stock
      tert-Butyl 2-cyanopyrrolidine-1-carboxylate|CS-W002838
      144688-70-0

    References

    • Hoshikawa, Tamaki; Yoshioka, Shun; Kamijo, Shin; Inoue, Masayuki Synthesis (Germany), 2013 , vol. 45, # 7 art. no. SS-2012-Z0984-FA, p. 874 - 887
  • Route2

    References

    • Tang; Qu; Xu; Ma; Chen, Shu-Hui; Li Synthetic Communications, 2007 , vol. 37, # 21 p. 3793 - 3799
  • Route3
    • null|null
      7677-24-9
    • In-stock
      tert-Butyl 2-methoxypyrrolidine-1-carboxylate|CS-0079687
      144688-69-7
    • ~73%
    • In-stock
      tert-Butyl 2-cyanopyrrolidine-1-carboxylate|CS-W002838
      144688-70-0

    References

    • Shono, Tatsuya; Terauchi, Jun; Kitayama, Kenji; Takeshima, Yo-Ichiro; Masumura, Yoshihiro Tetrahedron, 1992 , vol. 48, # 38 p. 8253 - 8262

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   53.33
  • LogP   1.90948
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   0

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