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(R)-tert-Butyl 3-formylpiperidine-1-carboxylate

  • CAS No. 194726-46-0

  • Cat. No. CS-0154727
  • Purity≥97%
  • MDL No.MFCD09953771

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

(R)-tert-Butyl 3-formylpiperidine-1-carboxylate|CS-0154727

Structure of 194726-46-0

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General Information

  • CAS No. 194726-46-0
  • Cat. No. CS-0154727
  • Purity ≥97%
  • MDL No. MFCD09953771
  • Storage -20°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₁H₁₉NO₃
  • Molecular Weight 213.27
  • Synonym(s) tert-Butyl (R)-3-formylpiperidine-1-carboxylate
  • SMILES CC(C)(C)OC(=O)N1CCC[C@H](C1)C=O

Description

(R)-tert-Butyl 3-formylpiperidine-1-carboxylate features a chiral piperidine core with a formyl group at the 3-position, offering a bench-stable, moisture-tolerant scaffold for asymmetric synthesis. This building block integrates readily into diverse molecular architectures through selective functionalization at the aldehyde site, enabling efficient access to bioactive alkaloid derivatives and pharmaceutical intermediates.

Application

(R)-tert-Butyl 3-formylpiperidine-1-carboxylate serves as a versatile chiral building block for the synthesis of bioactive piperidine derivatives. The formyl group enables direct functionalization via nucleophilic addition, while the tert-butyl carbamate provides robust protection and facile deprotection under mild acidic conditions. Its bench-stable nature and compatibility with standard coupling and reductive amination protocols make it ideal for medicinal chemistry applications requiring stereocontrolled access to pharmacologically relevant scaffolds.

Synthesis

  • Route1

    References

    • ELI LILLY AND COMPANY Patent: WO2005/118531 A1, 2005 ; Location in patent: Page/Page column 74 ; WO 2005/118531 A1
  • Route2

    References

    • PanThera Biopharma, LLC Patent: US2010/286125 A1, 2010 ; Location in patent: Page/Page column 30 ;
  • Route3
    • In-stock
      (R)-1-tert-Butyl 3-ethyl piperidine-1,3-dicarboxylate|CS-W010168
      194726-40-4
    • ~%
    • In-stock
      (R)-tert-Butyl 3-formylpiperidine-1-carboxylate|CS-0154727
      194726-46-0
    • null|null
      254905-64-1

    References

    • Novo Nordisk A/S Patent: US6919315 B1, 2005 ;

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS08,GHS09
Signal Word : Danger
UN#: 3082
Class : 9
Packing Group : Ⅲ
Hazard Statements : H302-H315-H319-H335-H372-H410
Precautionary Statements : P261-P264-P270-P271-P273-P280-P302+P352-P304+P340-P330-P362-P391-P405-P501

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Computational Chemistry Data

  • TPSA   46.61
  • LogP   1.8324
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   1

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