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CS-W001157 4
Total: USD 88.00

tert-Butyl 4-methylenepiperidine-1-carboxylate

  • CAS No. 159635-49-1

  • Cat. No. CS-W002803
  • Purity≥98%
  • MDL No.MFCD01632522

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

tert-Butyl 4-methylenepiperidine-1-carboxylate|CS-W002803

Structure of 159635-49-1

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General Information

  • CAS No. 159635-49-1
  • Cat. No. CS-W002803
  • Purity ≥98%
  • MDL No. MFCD01632522
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₁H₁₉NO₂
  • Molecular Weight 197.27
  • Synonym(s) tert-butyl 4-methylidenepiperidine-1-carboxylate
  • SMILES O=C(N1CCC(=C)CC1)OC(C)(C)C

Description

tert-Butyl 4-methylenepiperidine-1-carboxylate features a rigid piperidine core with a methylene bridge at the 4-position, enabling efficient cyclization and stereocontrol in synthetic routes. The tert-butyloxycarbonyl group provides stable protection under standard conditions, facilitating downstream functionalization while maintaining excellent solubility in organic solvents.

Application

tert-Butyl 4-methylenepiperidine-1-carboxylate serves as a versatile building block for the synthesis of piperidine-based scaffolds, enabling efficient access to medicinally relevant heterocycles. The methylene group facilitates selective functionalization via olefinic transformations, while the tert-butyl carbamate provides orthogonal protection and excellent bench stability. Its compatibility with standard coupling reactions, hydrogenation protocols, and acid-labile deprotection makes it ideal for iterative synthesis in medicinal chemistry and process development workflows.

Synthesis

  • Route1
    • null|null
      79099-07-3
    • ~10%
    • In-stock
      tert-Butyl 4-methylenepiperidine-1-carboxylate|CS-W002803
      159635-49-1

    References

    • ASTRAZENECA AB; NPS PHARMACEUTICALS, INC. Patent: WO2006/20879 A1, 2006 ; Location in patent: Page/Page column 101-102 ; WO 2006/020879 A1
  • Route2
    • null|null
      1779-49-3
    • null|null
      79099-07-3
    • ~94%
    • In-stock
      tert-Butyl 4-methylenepiperidine-1-carboxylate|CS-W002803
      159635-49-1

    References

    • BETA PHARMA CANADA INC.; WANG, Zhaoyin; LI, Lianhai; WANG, Zhigang Patent: WO2013/13308 A1, 2013 ; Location in patent: Paragraph 00196-00198 ; WO 2013/013308 A1
  • Route3
    • In-stock
      Methyltriphenylphosphonium iodide|CS-D1389
      2065-66-9
    • null|null
      79099-07-3
    • ~90%
    • In-stock
      tert-Butyl 4-methylenepiperidine-1-carboxylate|CS-W002803
      159635-49-1

    References

    • XENON PHARMACEUTICALS INC. Patent: WO2006/34338 A1, 2006 ; Location in patent: Page/Page column 50 ; WO 2006/034338 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

Quality Control

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Computational Chemistry Data

  • TPSA   29.54
  • LogP   2.5735
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   0

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