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tert-Butyl endo-3-amino-8-azabicyclo[3.2.1]octane-8-carboxylate

  • CAS No. 207405-68-3

  • Cat. No. CS-W005858
  • Purity≥97%
  • MDL No.MFCD18428077

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

tert-Butyl endo-3-amino-8-azabicyclo[3.2.1]octane-8-carboxylate|CS-W005858

Structure of 207405-68-3

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General Information

  • CAS No. 207405-68-3
  • Cat. No. CS-W005858
  • Purity ≥97%
  • MDL No. MFCD18428077
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₂H₂₂N₂O₂
  • Molecular Weight 226.32
  • Synonym(s) N-Boc-endo-3-aminotropane
  • SMILES O=C(N1[C@@]2([H])C[C@@H](N)C[C@]1([H])CC2)OC(C)(C)C

Description

This tert-butyl endo-3-amino-8-azabicyclo[3.2.1]octane-8-carboxylate features a rigid, electron-rich bicyclic scaffold with a bench-stable tert-butyl ester and a strategically positioned amino group. The endo configuration enhances stereochemical control in downstream transformations, enabling efficient incorporation into complex alkaloid frameworks and bioactive heterocycles under standard conditions.

Application

tert-Butyl endo-3-amino-8-azabicyclo[3.2.1]octane-8-carboxylate serves as a conformationally constrained, nitrogen-rich heterocyclic building block with well-defined stereochemistry. The tertiary amine and protected carboxylic acid functionalities enable straightforward derivatization in medicinal chemistry workflows. Its bench-stable tert-butyl ester facilitates purification, while the endo-amino group supports selective functionalization, making it a practical scaffold for targeted synthesis of bioactive molecules.

Synthesis

  • Route1
    • null|null
      207405-67-2
    • ~71%
    • In-stock
      tert-Butyl endo-3-amino-8-azabicyclo[3.2.1]octane-8-carboxylate|CS-W005858
      207405-68-3

    References

    • Journal of Medicinal Chemistry, , vol. 51, # 20 p. 6538 - 6546
  • Route2

    References

    • US2006/100426 A1, ; Page/Page column 18-19 ; US 20060100426 A1
  • Route3

    References

    • US2006/199839 A1, ; Page/Page column 23-24 ; US 20060199839 A1

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

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Computational Chemistry Data

  • TPSA   55.56
  • LogP   1.8756
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   0

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