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tert-Butyl (2S,4R)-4-hydroxy-2-hydroxymethylpyrrolidine-1-carboxylate

  • CAS No. 61478-26-0

  • Cat. No. CS-0021945
  • Purity≥97%
  • MDL No.MFCD02094386

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

tert-Butyl (2S,4R)-4-hydroxy-2-hydroxymethylpyrrolidine-1-carboxylate|CS-0021945

Structure of 61478-26-0

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General Information

  • CAS No. 61478-26-0
  • Cat. No. CS-0021945
  • Purity ≥97%
  • MDL No. MFCD02094386
  • Storage 4°C, protect from light, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₁₉NO₄
  • Molecular Weight 217.26
  • Synonym(s) None
  • SMILES OC[C@H]1N(C(OC(C)(C)C)=O)C[C@H](O)C1

Description

tert-Butyl (2S,4R)-4-hydroxy-2-hydroxymethylpyrrolidine-1-carboxylate features a stereochemically defined pyrrolidine core with orthogonal hydroxyl and hydroxymethyl groups. This bench-stable derivative enables direct incorporation into complex molecular architectures, serving as a key chiral building block for bioactive molecule synthesis.

Application

tert-Butyl (2S,4R)-4-hydroxy-2-hydroxymethylpyrrolidine-1-carboxylate serves as a stereochemically defined pyrrolidine building block for the synthesis of bioactive molecules. Its orthogonal functionality enables selective transformations at both the hydroxyl and hydroxymethyl groups, facilitating efficient access to complex heterocyclic scaffolds. The tert-butyl carbamate group provides stability and ease of removal under mild acidic conditions, supporting scalable synthesis and purification in medicinal chemistry workflows.

Synthesis

  • Route1

    References

    • Peterson, Mark L.; Vince, Robert Journal of Medicinal Chemistry, 1991 , vol. 34, # 9 p. 2787 - 2797
  • Route2

    References

    • BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BOEHRINGER INGELHEIM PHARMA GMBH and CO. KG Patent: WO2005/103031 A1, 2005 ; Location in patent: Page/Page column 70-71 ; WO 2005/103031 A1
  • Route3

    References

    • Kyowa Hakko Kirin Co., Ltd.; OTSUBO, Nobumasa; OKAZAKI, Shuko; TSUKUMO, Yukihito; IIDA, Kyoichiro; NAKOJI, Masayoshi Patent: EP2708540 A1, 2014 ; Location in patent: Paragraph 0305-0306 ;

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   70
  • LogP   0.349
  • H_Acceptors   4
  • H_Donors   2
  • Rotatable_Bonds   1

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