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tert-Butyl 6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate

  • CAS No. 114214-49-2

  • Cat. No. CS-D0109
  • Purity≥95%
  • MDL No.MFCD08691407

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

tert-Butyl 6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate|CS-D0109

Structure of 114214-49-2

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General Information

  • CAS No. 114214-49-2
  • Cat. No. CS-D0109
  • Purity ≥95%
  • MDL No. MFCD08691407
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₁₅NO₃
  • Molecular Weight 185.22
  • Synonym(s) 6-Oxa-3-azabicyclo[3.1.0]hexane-3-carboxylic Acid tert-Butyl Ester
  • SMILES O=C(OC(C)(C)C)N1CC(O2)C2C1

Description

tert-Butyl 6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate features a rigid, oxygen- and nitrogen-containing bicyclic scaffold that imparts high conformational stability. This bench-stable, moisture-tolerant building block integrates readily into complex molecular architectures, enabling efficient access to bioactive heterocycles through straightforward deprotection and functionalization pathways.

Application

tert-Butyl 6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate serves as a versatile bicyclic scaffold for medicinal chemistry, enabling the construction of constrained heterocyclic systems. Its stable tert-butyl ester facilitates straightforward deprotection, while the bridged oxazabicycle offers defined stereochemistry and rigidity. The molecule participates reliably in nucleophilic substitution and reductive amination, supporting efficient synthesis of complex nitrogen-containing frameworks under standard bench conditions.

Synthesis

  • Route1

    References

    • Bioorganic and Medicinal Chemistry Letters, , vol. 15, # 21 p. 4770 - 4773
  • Route2
    • null|null
      109-96-6
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      Di-tert-butyl dicarbonate|CS-0017817
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    • In-stock
      tert-Butyl 6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate|CS-D0109
      114214-49-2

    References

    • WO2005/26111 A2, ; Page/Page column 15 ; WO 2005/026111 A2
  • Route3
    • N-Boc-3-bromo-4-hydroxy-pyrrolidine|CS-0341747
      1017782-17-0
    • ~95%
    • In-stock
      tert-Butyl 6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate|CS-D0109
      114214-49-2

    References

    • WO2013/138210 A1, ; Paragraph 0184 ;

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   42.07
  • LogP   1.0045
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   0

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