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CS-W001157 4
Total: USD 88.00

tert-Butyl (3S)-3-(2-hydroxyethyl)morpholine-4-carboxylate

  • CAS No. 813433-76-0

  • Cat. No. CS-0048553
  • Purity≥95%
  • MDL No.None

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

tert-Butyl (3S)-3-(2-hydroxyethyl)morpholine-4-carboxylate|CS-0048553

Structure of 813433-76-0

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General Information

  • CAS No. 813433-76-0
  • Cat. No. CS-0048553
  • Purity ≥95%
  • MDL No. None
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₁H₂₁NO₄
  • Molecular Weight 231.29
  • Synonym(s) Tert-butyl 3-(2-hydroxyethyl)morpholine-4-carboxylate
  • SMILES CC(C)(C)OC(=O)N1CCOC[C@@H]1CCO

Description

tert-Butyl (3S)-3-(2-hydroxyethyl)morpholine-4-carboxylate is a chiral morpholine derivative featuring a stereodefined (3S) configuration and a pendant hydroxyethyl side chain. This combination delivers enhanced solubility and metabolic stability, enabling efficient incorporation into complex molecular scaffolds. The tert-butyl ester serves as a robust protecting group, removable under mild acidic conditions to reveal the carboxylic acid.

Application

tert-Butyl (3S)-3-(2-hydroxyethyl)morpholine-4-carboxylate serves as a versatile chiral building block for the synthesis of bioactive heterocycles and peptide mimetics. The morpholine core enables hydrogen bonding and solubility modulation, while the (3S)-stereochemistry provides defined spatial control in downstream transformations. The tert-butyl ester offers bench stability and facile deprotection under mild acidic conditions. The pendant hydroxyl group allows for selective derivatization or incorporation into complex molecular architectures via standard coupling reactions.

Synthesis

  • Route1
    • (S)-tert-Butyl 3-(2-ethoxy-2-oxoethyl)morpholine-4-carboxylate|CS-W000780
      761460-04-2
    • ~82%
    • In-stock
      tert-Butyl (3S)-3-(2-hydroxyethyl)morpholine-4-carboxylate|CS-0048553
      813433-76-0

    References

    • Pousset, Cyrille; Callens, Roland; Haddad, Mansour; Larcheveque, Marc Tetrahedron Asymmetry, 2004 , vol. 15, # 21 p. 3407 - 3412
  • Route2
    • Tert-butyl 3-(2-ethoxy-2-oxoethyl)morpholine-4-carboxylate|CS-0468801
      761460-02-0
    • ~%
    • In-stock
      tert-Butyl (3S)-3-(2-hydroxyethyl)morpholine-4-carboxylate|CS-0048553
      813433-76-0

    References

    • Synlett, , # 15 p. 2766 - 2770
  • Route3

    References

    • Tetrahedron Asymmetry, , vol. 15, # 21 p. 3407 - 3412

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-P330-P362-P405-P501

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Computational Chemistry Data

  • TPSA   59
  • LogP   1.0047
  • H_Acceptors   4
  • H_Donors   1
  • Rotatable_Bonds   2

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