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((S)-1-((S)-1-Phenylethyl)pyrrolidin-3-yl)methanol

  • CAS No. 173724-95-3

  • Cat. No. CS-0158258
  • Purity≥98%
  • MDL No.MFCD15526584

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

((S)-1-((S)-1-Phenylethyl)pyrrolidin-3-yl)methanol|CS-0158258

Structure of 173724-95-3

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General Information

  • CAS No. 173724-95-3
  • Cat. No. CS-0158258
  • Purity ≥98%
  • MDL No. MFCD15526584
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₃H₁₉NO
  • Molecular Weight 205.30
  • Synonym(s) (1S,3S)-phenylethylpyrrolidinylMethanol
  • SMILES C[C@@H](C1=CC=CC=C1)N2CC[C@@H](C2)CO

Description

This chiral pyrrolidinemethanol features a stereodefined (S)-1-phenylethyl group and an (S)-pyrrolidin-3-yl moiety, delivering high enantiomeric purity. The hydroxymethyl functionality enables straightforward derivatization, while the rigid, electron-rich framework supports its use in asymmetric synthesis and as a building block for bioactive molecules.

Application

((S)-1-((S)-1-Phenylethyl)pyrrolidin-3-yl)methanol serves as a chiral building block for asymmetric synthesis, featuring a stereogenic pyrrolidine core with pendant hydroxymethyl and benzylic centers. Its bench-stable nature and compatibility with standard functional group transformations enable efficient incorporation into bioactive scaffolds, particularly in medicinal chemistry campaigns requiring defined stereochemistry and enhanced solubility.

Synthesis

  • Route1
    • Methyl (S)-5-oxo-1-((S)-1-phenylethyl)pyrrolidine-3-carboxylate|CS-1636941
      146348-14-3
    • ~91%
    • In-stock
      ((S)-1-((S)-1-Phenylethyl)pyrrolidin-3-yl)methanol|CS-0158258
      173724-95-3

    References

    • WARNER-LAMBERT COMPANY LLC Patent: WO2005/49605 A1, 2005 ; Location in patent: Page/Page column 116; 117; 150 ;
  • Route2
    • (S)-5-Oxo-1-((S)-1-phenylethyl)pyrrolidine-3-carboxylic acid|CS-0053258
      173340-19-7
    • ~61%
    • In-stock
      ((S)-1-((S)-1-Phenylethyl)pyrrolidin-3-yl)methanol|CS-0158258
      173724-95-3

    References

    • Walker, Daniel P.; Acker, Brad A.; Jacobsen, E. Jon; Wishka, Donn G. Journal of Heterocyclic Chemistry, 2008 , vol. 45, # 1 p. 247 - 257
  • Route3

    References

    • Walker, Daniel Patrick; Piotrowski, David W.; Jacobsen, Eric Jon; Acker, Brad A.; Myers, Jason K.; Groppi JR., Vincent E. Patent: US2003/236279 A1, 2003 ;

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   23.47
  • LogP   2.0618
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   3

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