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CS-W001157 4
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tert-Butyl (trans-4-hydroxymethylcyclohexylmethyl)carbamate

  • CAS No. 172348-63-9

  • Cat. No. CS-0048501
  • Purity≥97%
  • MDL No.MFCD06657666

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

tert-Butyl (trans-4-hydroxymethylcyclohexylmethyl)carbamate|CS-0048501

Structure of 172348-63-9

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General Information

  • CAS No. 172348-63-9
  • Cat. No. CS-0048501
  • Purity ≥97%
  • MDL No. MFCD06657666
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₃H₂₅NO₃
  • Molecular Weight 243.35
  • Synonym(s) None
  • SMILES C(NC(OC(C)(C)C)=O)[C@@H]1CC[C@@H](CO)CC1

Description

tert-Butyl (trans-4-hydroxymethylcyclohexylmethyl)carbamate is a bench-stable, moisture-tolerant protecting group for primary amines, featuring a rigid trans-cyclohexyl scaffold that enhances stereochemical control. This carbamate integrates cleanly into complex molecular architectures, delivering predictable deprotection under mild acidic conditions.

Application

tert-Butyl (trans-4-hydroxymethylcyclohexylmethyl)carbamate serves as a stable, bench-friendly protecting group for primary amines, enabling selective functionalization in complex molecule synthesis. The trans-configured cyclohexyl scaffold provides defined stereochemistry and enhances conformational rigidity, while the pendant hydroxymethyl group offers a versatile handle for further derivatization via oxidation, protection, or coupling reactions. Its compatibility with standard deprotection conditions and robustness under diverse reaction conditions make it particularly useful in medicinal chemistry and natural product synthesis workflows.

Synthesis

  • Route1
    • trans-4-(Aminomethyl)cyclohexanemethanol hydrochloride|CS-0047770
      178972-33-3
    • In-stock
      Di-tert-butyl dicarbonate|CS-0017817
      24424-99-5
    • ~97%
    • In-stock
      tert-Butyl (trans-4-hydroxymethylcyclohexylmethyl)carbamate|CS-0048501
      172348-63-9

    References

    • AXYS Pharmaceuticals, Inc. Patent: US6022969 A1, 2000 ; US 6022969 A
  • Route2

    References

    • Joossens; Van Der Veken; Lambeir; Augustyns; Haemers Journal of Medicinal Chemistry, 2004 , vol. 47, # 10 p. 2411 - 2413
  • Route3

    References

    • Joossens; Van Der Veken; Lambeir; Augustyns; Haemers Journal of Medicinal Chemistry, 2004 , vol. 47, # 10 p. 2411 - 2413

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
Precautionary Statements : P264-P270-P330

Quality Control

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Computational Chemistry Data

  • TPSA   58.56
  • LogP   2.3098
  • H_Acceptors   3
  • H_Donors   2
  • Rotatable_Bonds   3

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