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tert-Butyl ((1R,2S)-2-aminocyclohexyl)carbamate

  • CAS No. 364385-54-6

  • Cat. No. CS-0137432
  • Molecule weight214.30
  • Purity≥97%
  • MDL No.None

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

tert-Butyl ((1R,2S)-2-aminocyclohexyl)carbamate|CS-0137432

Structure of 364385-54-6

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General Information

  • CAS No. 364385-54-6
  • Cat. No. CS-0137432
  • Purity ≥97%
  • MDL No. None
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₁H₂₂N₂O₂
  • Molecular Weight 214.30
  • Synonym(s) tert-butyl N-[(1R,2S)-2-aminocyclohexyl]carbamate
  • SMILES O=C(OC(C)(C)C)N[C@H]1[C@@H](N)CCCC1

Description

tert-Butyl ((1R,2S)-2-aminocyclohexyl)carbamate is a chiral auxiliary featuring a stereodefined cyclohexylamine scaffold with a bench-stable tert-butoxycarbonyl (Boc) protecting group. This configuration enables selective functionalization in asymmetric synthesis, particularly in the construction of nitrogen-containing heterocycles and bioactive molecules. The rigid, trans-fused ring system facilitates stereocontrol during downstream transformations.

Application

tert-Butyl ((1R,2S)-2-aminocyclohexyl)carbamate serves as a versatile chiral building block in medicinal chemistry, enabling stereoselective synthesis of cyclohexyl-containing bioactive molecules. The protected amine functionality offers excellent bench stability and facilitates straightforward deprotection under mild acidic conditions. Its rigid cyclohexyl scaffold provides defined spatial orientation, enhancing predictability in conformationally constrained target design.

Synthesis

  • Route1
    • null|null
      603128-65-0
    • ~69%
    • In-stock
      tert-Butyl ((1R,2S)-2-aminocyclohexyl)carbamate|CS-0137432
      364385-54-6

    References

    • ASTRAZENECA AB Patent: US2007/287695 A1, 2007 ; Location in patent: Page/Page column 14; 56 ; US 20070287695 A1
  • Route2

    References

    • Journal of Organic Chemistry, , vol. 69, # 6 p. 1858 - 1865
  • Route3
    • null|null
      603128-64-9
    • ~%
    • In-stock
      tert-Butyl ((1R,2S)-2-aminocyclohexyl)carbamate|CS-0137432
      364385-54-6

    References

    • Journal of Organic Chemistry, , vol. 69, # 6 p. 1858 - 1865

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H315-H319
Precautionary Statements : P264-P280-P302+P352-P362

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Computational Chemistry Data

  • TPSA   64.35
  • LogP   1.781
  • H_Acceptors   3
  • H_Donors   2
  • Rotatable_Bonds   1

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