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tert-Butyl 2-cyano-7-azaspiro[3.5]nonane-7-carboxylate

  • CAS No. 203662-66-2

  • Cat. No. CS-0036790
  • Purity≥97%
  • MDL No.MFCD12198800

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

tert-Butyl 2-cyano-7-azaspiro[3.5]nonane-7-carboxylate|CS-0036790

Structure of 203662-66-2

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General Information

  • CAS No. 203662-66-2
  • Cat. No. CS-0036790
  • Purity ≥97%
  • MDL No. MFCD12198800
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₄H₂₂N₂O₂
  • Molecular Weight 250.34
  • Synonym(s) None
  • SMILES N#CC1CC2(CCN(C(=O)OC(C)(C)C)CC2)C1

Description

tert-Butyl 2-cyano-7-azaspiro[3.5]nonane-7-carboxylate is a sterically encumbered spirocyclic building block featuring a cyano group and a tert-butyl ester, enabling efficient access to complex nitrogen-containing scaffolds. The spiro architecture imparts rigidity and distinct stereochemical control, while the cyano moiety offers versatility in downstream functionalization. This compound exhibits bench-stable handling characteristics and compatibility with standard organic transformations.

Application

tert-Butyl 2-cyano-7-azaspiro[3.5]nonane-7-carboxylate serves as a versatile spirocyclic building block for medicinal chemistry, enabling efficient access to complex nitrogen-containing scaffolds. The pendant nitrile group facilitates downstream transformations such as amidation, hydrolysis, or cyclization, while the tert-butyl ester supports orthogonal deprotection. Its rigid spiro structure enhances conformational control, and the molecule exhibits excellent bench stability and ease of purification—ideal for modular synthesis in API development.

Synthesis

  • Route1
    • null|null
      773837-37-9
    • tert-Butyl 2-((methylsulfonyl)oxy)-7-azaspiro[3.5]nonane-7-carboxylate|CS-0617066
      614729-59-8
    • ~67%
    • In-stock
      tert-Butyl 2-cyano-7-azaspiro[3.5]nonane-7-carboxylate|CS-0036790
      203662-66-2

    References

    • Pfizer Inc. Patent: US2010/113465 A1, 2010 ; Location in patent: Page/Page column 24 ; US 20100113465 A1
  • Route2
    • null|null
      38622-91-2
    • In-stock
      tert-Butyl 2-oxo-7-azaspiro[3.5]nonane-7-carboxylate|CS-W007836
      203661-69-2
    • ~32%
    • In-stock
      tert-Butyl 2-cyano-7-azaspiro[3.5]nonane-7-carboxylate|CS-0036790
      203662-66-2

    References

    • Kaneko, Toshihiko; Clark, Richard S. J.; Ohi, Norihito; Ozaki, Fumihiro; Kawahara, Tetsuya; Kamada, Atsushi; Okano, Kazuo; Yokohama, Hiromitsu; Ohkuro, Masayoshi; Muramoto, Kenzo; Takenaka, Osamu; Kobayashi, Seiichi Chemical and Pharmaceutical Bulletin, 2004 , vol. 52, # 6 p. 675 - 687
  • Route3

    References

    • Brown, Dean G.; Bernstein, Peter R.; Griffin, Andrew; Wesolowski, Steve; Labrecque, Denis; Tremblay, Maxime C.; Sylvester, Mark; Mauger, Russell; Edwards, Phillip D.; Throner, Scott R.; Folmer, James J.; Cacciola, Joseph; Scott, Clay; Lazor, Lois A.; Pourashraf, Mehrnaz; Santhakumar, Vijayaratnam; Potts, William M.; Sydserff, Simon; Giguere, Pascall; Levesque, Carine; Dasser, Mohammed; Groblewski, Thierry Journal of Medicinal Chemistry, 2014 , vol. 57, # 3 p. 733 - 758

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-P501

Quality Control

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Computational Chemistry Data

  • TPSA   53.33
  • LogP   2.93728
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   0

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