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CS-W001157 4
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(2R)-2-[Bis[3,5-bis(trifluoromethyl)phenyl]-[(tert-butyldimethylsilyl)oxy]methyl]pyrrolidine

  • CAS No. 1146629-74-4

  • Cat. No. CS-0003924
  • Purity≥96%
  • MDL No.MFCD15528963

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

(2R)-2-[Bis[3,5-bis(trifluoromethyl)phenyl]-[(tert-butyldimethylsilyl)oxy]methyl]pyrrolidine|CS-0003924

Structure of 1146629-74-4

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General Information

  • CAS No. 1146629-74-4
  • Cat. No. CS-0003924
  • Purity ≥96%
  • MDL No. MFCD15528963
  • Storage 4°C, protect from light, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₂₇H₂₉F₁₂NOSi
  • Molecular Weight 639.59
  • Synonym(s) (R)-2-(Bis(3,5-bis(trifluoromethyl)phenyl)-((tert-butyldimethylsilyl)oxy)methyl)pyrrolidine
  • SMILES C[Si](C)(C(C)(C)C)OC(C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1)([C@@H]2NCCC2)C3=CC(C(F)(F)F)=CC(C(F)(F)F)=C3

Description

This chiral pyrrolidine scaffold features a sterically hindered silyl-protected hydroxymethyl group at the 2-position, enabling selective functionalization in asymmetric synthesis. The bis(trifluoromethyl)phenyl substituents confer enhanced electron-withdrawing character and improved solubility in organic media, facilitating use under standard bench conditions.

Application

(2R)-2-[Bis[3,5-bis(trifluoromethyl)phenyl]-[(tert-butyldimethylsilyl)oxy]methyl]pyrrolidine serves as a robust chiral auxiliary in asymmetric synthesis, leveraging its sterically encumbered pyrrolidine core and silyl-protected hydroxymethyl group. The trifluoromethyl-substituted aryl moieties enhance stability and modulate electronic properties, while the tert-butyldimethylsilyl (TBS) ether enables selective deprotection and orthogonal functionalization. This scaffold facilitates stereoselective C–C bond formation and functions reliably in multistep sequences requiring bench-stable, high-purity intermediates for medicinal chemistry and process development.

Synthesis

  • Route1
    • In-stock
      (R)-Bis(3,5-bis(trifluoromethyl)phenyl)(pyrrolidin-2-yl)methanol|CS-B0073
      948595-00-4
    • null|null
      69739-34-0
    • ~92%
    • In-stock
      (2R)-2-[Bis[3,5-bis(trifluoromethyl)phenyl]-[(tert-butyldimethylsilyl)oxy]methyl]pyrrolidine|CS-0003924
      1146629-74-4

    References

    • Zhou, Jiacheng; Liu, Pingli; Lin, Qiyan; Metcalf, Brian W.; Meloni, David; Pan, Yongchun; Xia, Michael; Li, Mei; Yue, Tai-Yuen; Rodgers, James D.; Wang, Haisheng Patent: US2010/190981 A1, 2010 ; Location in patent: Page/Page column 67-68 ; US 20100190981 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-P330-P362+P364-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   21.26
  • LogP   9.7792
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   5

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