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CS-W001157 4
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tert-Butyl 9-oxo-3-azaspiro[5.5]undecane-3-carboxylate

  • CAS No. 873924-08-4

  • Cat. No. CS-0036506
  • Purity≥96%
  • MDL No.MFCD12198558

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

tert-Butyl 9-oxo-3-azaspiro[5.5]undecane-3-carboxylate|CS-0036506

Structure of 873924-08-4

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General Information

  • CAS No. 873924-08-4
  • Cat. No. CS-0036506
  • Purity ≥96%
  • MDL No. MFCD12198558
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₅H₂₅NO₃
  • Molecular Weight 267.37
  • Synonym(s) None
  • SMILES O=C(OC(C)(C)C)N1CCC2(CCC(=O)CC2)CC1

Description

tert-Butyl 9-oxo-3-azaspiro[5.5]undecane-3-carboxylate features a rigid spirocyclic scaffold with a ketone at C9 and a protected amine at N3, enabling direct functionalization at the 3-position. This configuration supports efficient access to complex nitrogen-containing polycycles in medicinal chemistry and natural product synthesis.

Application

tert-Butyl 9-oxo-3-azaspiro[5.5]undecane-3-carboxylate serves as a versatile spirocyclic building block for the synthesis of complex nitrogen-containing scaffolds. The ketone at C9 enables selective reductions, enolate formations, and nucleophilic additions, while the protected amine at N3 provides orthogonal reactivity. Its tert-butyl ester facilitates mild deprotection under acidic conditions, and the rigid spirocyclic framework imparts conformational control, making it valuable in medicinal chemistry and target-oriented synthesis.

Synthesis

  • Route1
    • tert-Butyl 9-oxo-3-azaspiro[5.5]undec-10-ene-3-carboxylate|CS-0037763
      873924-07-3
    • ~99%
    • In-stock
      tert-Butyl 9-oxo-3-azaspiro[5.5]undecane-3-carboxylate|CS-0036506
      873924-08-4

    References

    • Gruenenthal GmbH Patent: US2010/249095 A1, 2010 ; Location in patent: Page/Page column 127 ; US 20100249095 A1
  • Route2
    • In-stock
      Di-tert-butyl dicarbonate|CS-0017817
      24424-99-5
    • Benzyl 9-oxo-3-azaspiro[5.5]Undec-7-ene-3-carboxylate|CS-0449389
      189333-18-4
    • ~61%
    • In-stock
      tert-Butyl 9-oxo-3-azaspiro[5.5]undecane-3-carboxylate|CS-0036506
      873924-08-4

    References

    • Boivin, Roch; Carlson, Eric; Endo, Atsushi; Hansen, Hans; Hawkins, Lynn D.; Ishizaka, Sally; Mackey, Matthew; Narayan, Sridhar; Satoh, Takashi; Schiller, Shawn Patent: US2013/324547 A1, 2013 ; Location in patent: Paragraph 0500 ;
  • Route3

    References

    • GRUENENTHAL GmbH Patent: US2010/113417 A1, 2010 ; Location in patent: Page/Page column 38 ;

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   3.1468
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   0

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