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

  • CAS No. 203661-69-2

  • Cat. No. CS-W007836
  • Purity≥97%
  • MDL No.MFCD12198552

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

tert-Butyl 2-oxo-7-azaspiro[3.5]nonane-7-carboxylate|CS-W007836

Structure of 203661-69-2

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General Information

  • CAS No. 203661-69-2
  • Cat. No. CS-W007836
  • Purity ≥97%
  • MDL No. MFCD12198552
  • Storage 4°C, sealed storage, away from moisture
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₃H₂₁NO₃
  • Molecular Weight 239.32
  • Synonym(s) None
  • SMILES O=C(OC(C)(C)C)N1CCC2(CC(=O)C2)CC1

Description

tert-Butyl 2-oxo-7-azaspiro[3.5]nonane-7-carboxylate is a sterically hindered spirocyclic lactam precursor featuring a bench-stable tert-butyl ester and a ketone at the 2-position. This scaffold integrates readily into complex heterocycles, enabling efficient access to nitrogen-rich frameworks in medicinal chemistry and natural product synthesis.

Application

tert-Butyl 2-oxo-7-azaspiro[3.5]nonane-7-carboxylate serves as a versatile spirocyclic scaffold for medicinal chemistry and catalytic synthesis. The molecule features a stable, sterically hindered spirocyclic core with orthogonal functional groups: a ketone at C2 and a tert-butyl ester at C7. This combination enables selective transformations including reductive amination, nucleophilic addition, and transition-metal-catalyzed coupling reactions. Its bench-stable nature and compatibility with standard purification methods make it ideal for iterative synthesis of complex heterocycles and drug-like scaffolds.

Synthesis

  • Route1
    • tert-Butyl 1,1-dichloro-2-oxo-7-azaspiro[3.5]nonane-7-carboxylate|CS-0037785
      396653-31-9
    • ~98%
    • In-stock
      tert-Butyl 2-oxo-7-azaspiro[3.5]nonane-7-carboxylate|CS-W007836
      203661-69-2

    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
  • Route2
    • In-stock
      tert-Butyl 4-methylenepiperidine-1-carboxylate|CS-W002803
      159635-49-1
    • null|null
      76-02-8
    • ~14%
    • In-stock
      tert-Butyl 2-oxo-7-azaspiro[3.5]nonane-7-carboxylate|CS-W007836
      203661-69-2

    References

    • BETA PHARMA CANADA INC.; WANG, Zhaoyin; LI, Lianhai; WANG, Zhigang Patent: WO2013/13308 A1, 2013 ; Location in patent: Paragraph 00199-00201 ; WO 2013/013308 A1
  • Route3

    References

    • Chemical and Pharmaceutical Bulletin, , vol. 52, # 6 p. 675 - 687

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   46.61
  • LogP   2.3666
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   0

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