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tert-Butyl (2S)-4,4-difluoro-2-(hydroxymethyl)pyrrolidine-1-carboxylate

  • CAS No. 215918-21-1

  • Cat. No. CS-0036170
  • Molecule weight237.24
  • Purity≥97%
  • MDL No.None

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

tert-Butyl (2S)-4,4-difluoro-2-(hydroxymethyl)pyrrolidine-1-carboxylate|CS-0036170

Structure of 215918-21-1

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General Information

  • CAS No. 215918-21-1
  • Cat. No. CS-0036170
  • Purity ≥97%
  • MDL No. None
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₁₇F₂NO₃
  • Molecular Weight 237.24
  • Synonym(s) (S)-tert-Butyl 4,4-difluoro-2-(hydroxymethyl)-pyrrolidine-1-carboxylate
  • SMILES CC(C)(C)OC(=O)N1CC(C[C@H]1CO)(F)F

Description

tert-Butyl (2S)-4,4-difluoro-2-(hydroxymethyl)pyrrolidine-1-carboxylate is a stereodefined pyrrolidine derivative featuring a bench-stable tert-butyl carbamate protecting group and a hydroxymethyl side chain. The geminal difluoride moiety imparts enhanced metabolic stability and modulates electronic properties, enabling efficient incorporation into bioactive scaffolds. This building block facilitates the synthesis of fluorinated peptidomimetics and kinase inhibitors with improved membrane permeability.

Application

tert-Butyl (2S)-4,4-difluoro-2-(hydroxymethyl)pyrrolidine-1-carboxylate serves as a stereochemically defined building block for fluorinated pyrrolidine scaffolds. The difluoro substitution enhances metabolic stability and modulates conformational flexibility, while the hydroxymethyl group enables downstream functionalization via oxidation or derivatization. The tert-butyl carbamate protects the nitrogen during synthesis, offering bench stability and ease of purification in multi-step sequences.

Synthesis

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    References

    • Limpachayaporn, Panupun; Riemann, Burkhard; Kopka, Klaus; Schober, Otmar; Schaefers, Michael; Haufe, Guenter European Journal of Medicinal Chemistry, 2013 , vol. 64, p. 562 - 578
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    References

    • Bristol-Myers Squibb Company Patent: US2011/82165 A1, 2011 ; Location in patent: Page/Page column 29-30 ;
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    References

    • SUNSHINE LAKE PHARMA CO., LTD.; ZHANG, Yingjun; ZHANG, Jiancun; XIE, Hongming; REN, Qingyun; TAN, Yumei; LUO, Huichao Patent: WO2014/19344 A1, 2014 ;

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   1.6234
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   1

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