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CS-W001157 4
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Benzyl 6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate

  • CAS No. 31865-25-5

  • Cat. No. CS-0049819
  • Purity≥98%
  • MDL No.None

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

Benzyl 6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate|CS-0049819

Structure of 31865-25-5

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General Information

  • CAS No. 31865-25-5
  • Cat. No. CS-0049819
  • Purity ≥98%
  • MDL No. None
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₂H₁₃NO₃
  • Molecular Weight 219.24
  • Synonym(s) N-Cbz-6-oxa-3-azabicyclo[3.1.0]hexane
  • SMILES O=C(OCC1=CC=CC=C1)N1CC2OC2C1

Description

Benzyl 6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate is a conformationally constrained heterocyclic scaffold featuring a bridged oxazabicycle with a pendant benzyl ester. This stable, moisture-tolerant building block integrates readily into complex molecular architectures, enabling efficient access to bioactive analogs in medicinal chemistry campaigns.

Application

Benzyl 6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate serves as a versatile bicyclic scaffold for medicinal chemistry and synthetic methodology development. The molecule features a constrained 3-azabicyclo[3.1.0]hexane core with orthogonal functional handles: a benzyl ester for selective hydrolysis and a remote ether oxygen enabling conformational control. Its bench-stable nature, compatibility with standard coupling reactions, and utility in constructing nitrogen-containing heterocycles make it a practical building block for targeted library synthesis and API intermediate development.

Synthesis

  • Route1

    References

    • Pfizer Inc Patent: US2005/256310 A1, 2005 ; Location in patent: Page/Page column 12 ;
  • Route2
    • In-stock
      Benzyl 2,5-dihydro-1H-pyrrole-1-carboxylate|CS-W002856
      31970-04-4
    • null|null
      937-14-4
    • ~95%
    • In-stock
      Benzyl 6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate|CS-0049819
      31865-25-5

    References

    • NYCOMED GMBH; BARTELS, Bjoern; WEINBRENNER, Steffen; MARX, Degenhard; DIEFENBACH, Joerg; DUNKERN, Torsten; MENGE, Wiro M.P.B.; CHRISTIAANS, Johannes A. M. Patent: WO2010/15588 A1, 2010 ; Location in patent: Page/Page column 94 ; WO 2010/015588 A1
  • Route3
    • null|null
      25070-76-2
    • ~%
    • In-stock
      Benzyl 6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate|CS-0049819
      31865-25-5

    References

    • Kamal, Ahmed; Shaik, Ahmad Ali; Sandbhor, Mahendra; Malik, M. Shaheer; Kaga, Harumi Tetrahedron Letters, 2004 , vol. 45, # 43 p. 8057 - 8059

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   1.4062
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   2

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