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tert-Butyl (3S,4R)-3-fluoro-4-hydroxypiperidine-1-carboxylate

  • CAS No. 1174020-40-6

  • Cat. No. CS-0047556
  • Molecule weight219.25
  • Purity≥97%
  • MDL No.MFCD18632748

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

tert-Butyl (3S,4R)-3-fluoro-4-hydroxypiperidine-1-carboxylate|CS-0047556

Structure of 1174020-40-6

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General Information

  • CAS No. 1174020-40-6
  • Cat. No. CS-0047556
  • Purity ≥97%
  • MDL No. MFCD18632748
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₁₈FNO₃
  • Molecular Weight 219.25
  • Synonym(s) (3S,4R)-tert-Butyl 3-fluoro-4-hydroxypiperidine-1-carboxylate
  • SMILES O=C(N1C[C@H](F)[C@H](O)CC1)OC(C)(C)C

Description

This tert-butyl (3S,4R)-3-fluoro-4-hydroxypiperidine-1-carboxylate features a stereochemically defined piperidine scaffold with fluorine and hydroxyl groups positioned for precise molecular integration. The bench-stable tert-butyl carbamate protects the amine during synthetic manipulations, enabling efficient incorporation into bioactive molecules. This configuration supports conformational rigidity in target compounds, enhancing binding affinity and metabolic stability.

Application

tert-Butyl (3S,4R)-3-fluoro-4-hydroxypiperidine-1-carboxylate serves as a stereochemically defined building block for fluorinated piperidine scaffolds. The protected hydroxyl group enables selective functionalization, while the fluorine substituent imparts metabolic stability and modulates electronic properties. This intermediate exhibits excellent bench stability and facilitates downstream transformations including coupling reactions and cyclizations, making it valuable in medicinal chemistry and API synthesis.

Synthesis

  • Route1
    • In-stock
      tert-Butyl (3S)-3-fluoro-4-oxopiperidine-1-carboxylate|CS-0048542
      1450879-67-0
    • ~76%
    • In-stock
      tert-Butyl (3S,4R)-3-fluoro-4-hydroxypiperidine-1-carboxylate|CS-0047556
      1174020-40-6

    References

    • Shaw, Simon J.; Goff, Dane A.; Boralsky, Luke A.; Irving, Mark; Singh, Rajinder Journal of Organic Chemistry, 2013 , vol. 78, # 17 p. 8892 - 8897
  • Route2

    References

    • PFIZER INC.; GUIMARAES, Cristiano Ruch Werneck; MASCITTI, Vincent; MCCLURE, Kim Francis; MUNCHHOF, Michael John; ROBINSON, Ralph Pelton, Jr. Patent: WO2011/36576 A1, 2011 ; WO 2011/036576 A1
  • Route3
    • tert-Butyl 4-((trimethylsilyl)oxy)-5,6-dihydropyridine-1(2H)-carboxylate|CS-W001500
      211108-48-4
    • ~%
    • In-stock
      tert-Butyl (3S,4R)-3-fluoro-4-hydroxypiperidine-1-carboxylate|CS-0047556
      1174020-40-6
    • In-stock
      tert-Butyl (3R,4S)-3-fluoro-4-hydroxypiperidine-1-carboxylate|CS-0048560
      1174020-42-8

    References

    • PFIZER INC.; GUIMARAES, Cristiano Ruch Werneck; MASCITTI, Vincent; MCCLURE, Kim Francis; MUNCHHOF, Michael John; ROBINSON, Ralph Pelton, Jr. Patent: WO2011/36576 A1, 2011 ; WO 2011/036576 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   49.77
  • LogP   1.3262
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   0

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