Cas no 1260893-18-2 (Tert-butyl 4-(hydroxymethyl)-4-(trifluoromethyl)piperidine-1-carboxylate)

Tert-butyl 4-(hydroxymethyl)-4-(trifluoromethyl)piperidine-1-carboxylate is a versatile intermediate in organic synthesis, particularly valuable for pharmaceutical and agrochemical applications. Its structure features a piperidine core with a hydroxymethyl and trifluoromethyl group at the 4-position, along with a Boc (tert-butoxycarbonyl) protecting group, enhancing stability and reactivity control. The trifluoromethyl group imparts unique electronic and steric properties, while the hydroxymethyl functionality allows for further derivatization. The Boc group facilitates selective deprotection under mild acidic conditions, making it suitable for multi-step syntheses. This compound is particularly useful in the development of bioactive molecules, offering a balance of reactivity and stability for advanced synthetic routes.
Tert-butyl 4-(hydroxymethyl)-4-(trifluoromethyl)piperidine-1-carboxylate structure
1260893-18-2 structure
Product Name:Tert-butyl 4-(hydroxymethyl)-4-(trifluoromethyl)piperidine-1-carboxylate
CAS No:1260893-18-2
MF:C12H20F3NO3
MW:283.287314414978
MDL:MFCD11848162
CID:4565608
PubChem ID:53404347
Update Time:2025-11-01

Tert-butyl 4-(hydroxymethyl)-4-(trifluoromethyl)piperidine-1-carboxylate Chemical and Physical Properties

Names and Identifiers

    • tert-butyl 4-(hydroxymethyl)-4-(trifluoromethyl)piperidine-1-carboxylate
    • SB15561
    • P11225
    • 1-Boc-4-(hydroxymethyl)-4-(trifluoromethyl)piperidine
    • t-Butyl 4-(hydroxymethyl)-4-(trifluoromethyl)piperidine-1-carboxylate
    • 1-Piperidinecarboxylic acid, 4-(hydroxymethyl)-4-(trifluoromethyl)-, 1,1-dimethylethyl ester
    • CS-0056561
    • tert-butyl4-(hydroxymethyl)-4-(trifluoromethyl)piperidine-1-carboxylate
    • 1260893-18-2
    • SCHEMBL23536114
    • EN300-6201498
    • AS-80136
    • MFCD11848162
    • Tert-butyl 4-(hydroxymethyl)-4-(trifluoromethyl)piperidine-1-carboxylate
    • MDL: MFCD11848162
    • Inchi: 1S/C12H20F3NO3/c1-10(2,3)19-9(18)16-6-4-11(8-17,5-7-16)12(13,14)15/h17H,4-8H2,1-3H3
    • InChI Key: CXJLSBIXCPFDGX-UHFFFAOYSA-N
    • SMILES: FC(C1(CO)CCN(C(=O)OC(C)(C)C)CC1)(F)F

Computed Properties

  • Exact Mass: 283.13952799g/mol
  • Monoisotopic Mass: 283.13952799g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 6
  • Heavy Atom Count: 19
  • Rotatable Bond Count: 3
  • Complexity: 328
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 2.1
  • Topological Polar Surface Area: 49.8

Tert-butyl 4-(hydroxymethyl)-4-(trifluoromethyl)piperidine-1-carboxylate Pricemore >>

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Additional information on Tert-butyl 4-(hydroxymethyl)-4-(trifluoromethyl)piperidine-1-carboxylate

Recent Advances in the Application of Tert-butyl 4-(hydroxymethyl)-4-(trifluoromethyl)piperidine-1-carboxylate (CAS: 1260893-18-2) in Chemical Biology and Pharmaceutical Research

The compound Tert-butyl 4-(hydroxymethyl)-4-(trifluoromethyl)piperidine-1-carboxylate (CAS: 1260893-18-2) has recently emerged as a key intermediate in the synthesis of biologically active molecules, particularly in the development of novel pharmaceuticals targeting central nervous system (CNS) disorders and metabolic diseases. This piperidine derivative, characterized by its trifluoromethyl and hydroxymethyl functional groups, offers unique physicochemical properties that enhance drug-like characteristics, including improved metabolic stability and blood-brain barrier permeability.

Recent studies have highlighted the role of this compound in the synthesis of potent gamma-aminobutyric acid (GABA) receptor modulators. A 2023 publication in the Journal of Medicinal Chemistry demonstrated its utility as a building block for the development of next-generation anxiolytics with reduced side-effect profiles. The trifluoromethyl group, in particular, was shown to significantly enhance binding affinity to GABA-A receptor subtypes while the hydroxymethyl group facilitated further structural modifications.

In the field of protease inhibitor development, researchers at several major pharmaceutical companies have incorporated this piperidine derivative into novel scaffolds targeting viral proteases. The compound's structural flexibility allows for the introduction of various pharmacophores while maintaining optimal spatial orientation for target binding. A recent patent application (WO2023051234) describes its use in the synthesis of covalent inhibitors of SARS-CoV-2 main protease, showing promising in vitro activity against multiple variants of concern.

The synthetic accessibility of 1260893-18-2 has been significantly improved through recent methodological advances. A 2024 report in Organic Process Research & Development detailed a scalable, continuous-flow synthesis route that achieves >90% yield with excellent enantioselectivity. This development is particularly important as demand for the compound has increased substantially in both academic and industrial research settings.

From a medicinal chemistry perspective, the presence of both the hydroxymethyl and trifluoromethyl groups on the piperidine ring provides multiple vectors for structure-activity relationship (SAR) exploration. Computational studies published in late 2023 suggest that these functional groups participate in unique halogen bonding interactions with biological targets, potentially explaining the enhanced potency observed in several compound series derived from this intermediate.

Looking forward, the application of 1260893-18-2 appears poised for expansion into additional therapeutic areas. Preliminary data presented at the 2024 American Chemical Society National Meeting demonstrated its incorporation into novel radiopharmaceuticals for positron emission tomography (PET) imaging, leveraging the fluorine atoms for 18F-labeling. This dual utility as both a synthetic intermediate and potential imaging agent underscores the compound's growing importance in chemical biology and pharmaceutical research.

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