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di-tert-Butyl 2-(hydroxymethyl)piperazine-1,4-dicarboxylate

  • CAS No. 143540-05-0

  • Cat. No. CS-0128668
  • Purity≥95%
  • MDL No.MFCD09908093

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

di-tert-Butyl 2-(hydroxymethyl)piperazine-1,4-dicarboxylate|CS-0128668

Structure of 143540-05-0

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General Information

  • CAS No. 143540-05-0
  • Cat. No. CS-0128668
  • Purity ≥95%
  • MDL No. MFCD09908093
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₅H₂₈N₂O₅
  • Molecular Weight 316.39
  • Synonym(s) Di-tert-butyl 2-(hydroxymethyl)-piperazine-1,4-dicarboxylate
  • SMILES O=C(N1C(CO)CN(C(OC(C)(C)C)=O)CC1)OC(C)(C)C

Description

di-tert-Butyl 2-(hydroxymethyl)piperazine-1,4-dicarboxylate features a sterically shielded piperazine core with two tert-butyl ester groups and a pendant hydroxymethyl handle. This combination delivers enhanced stability and solubility in organic media, enabling straightforward functionalization in synthetic sequences. The protected hydroxyl group facilitates selective derivatization while maintaining structural integrity under standard conditions.

Application

di-tert-Butyl 2-(hydroxymethyl)piperazine-1,4-dicarboxylate serves as a versatile building block for piperazine-based scaffolds in medicinal chemistry. The protected piperazine core enables orthogonal functionalization, while the hydroxymethyl group facilitates downstream derivatization via oxidation or substitution. Bench-stable and readily purified by standard chromatography, it functions effectively in multi-step syntheses requiring precise control over nitrogen functionality and stereochemical integrity.

Synthesis

  • Route1
    • null|null
      543-27-1
    • In-stock
      1,4-Bis(tert-butoxycarbonyl)piperazine-2-carboxylic acid|CS-W008592
      181955-79-3
    • ~81%
    • In-stock
      di-tert-Butyl 2-(hydroxymethyl)piperazine-1,4-dicarboxylate|CS-0128668
      143540-05-0

    References

    • Matsumoto, Takahiro; Kamo, Izumi; Nomura, Izumi Patent: US2009/318412 A1, 2009 ; Location in patent: Page/Page column 34 ; US 20090318412 A1
  • Route2

    References

    • AGIOS PHARMACEUTICALS, INC.; CAO, Sheldon; POPOVICI-MULLER, Janeta; SALITURO, Francesco G.; SAUNDERS, Jeffrey; TAN, Xuefei; TRAVINS, Jeremy; YAN, Shunqi; YE, Zhixiong Patent: WO2012/171506 A1, 2012 ; Location in patent: Page/Page column 113 ; WO 2012/171506 A1
  • Route3

    References

    • Clark, Roger B.; Elbaum, Daniel Tetrahedron, 2007 , vol. 63, # 14 p. 3057 - 3065

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-P280-P302+P352

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Computational Chemistry Data

  • TPSA   79.31
  • LogP   1.8351
  • H_Acceptors   5
  • H_Donors   1
  • Rotatable_Bonds   1

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