948595-00-4

Usage

Uses

Used in Organic Synthesis:
(R)-bis(3,5-bis(trifluoroMethyl)phenyl)(pyrrolidin-2-yl)Methanol is utilized as a reagent in organic synthesis, where its unique structure and properties facilitate the creation of complex organic molecules. Its role in this industry is pivotal for the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals that require precise molecular structures.
Used in Pharmaceutical Research:
In the pharmaceutical sector, (R)-bis(3,5-bis(trifluoroMethyl)phenyl)(pyrrolidin-2-yl)Methanol serves as a key component in research, particularly in the development of chiral catalysts and ligands. Its chiral nature is essential for the creation of enantioselective catalysts, which are critical for producing single enantiomers of chiral drugs, thereby enhancing the efficacy and safety of medications.
Used in Asymmetric Synthesis:
(R)-bis(3,5-bis(trifluoroMethyl)phenyl)(pyrrolidin-2-yl)Methanol is employed as a chiral auxiliary or a building block in asymmetric synthesis. Its use in this capacity is instrumental for achieving the desired enantioselectivity and stereochemistry in the synthesis of biologically active compounds, which is crucial for their biological activity and pharmacological properties.
Used in Chemical and Biological Applications:
Due to its potentially low toxicity and high stability, (R)-bis(3,5-bis(trifluoroMethyl)phenyl)(pyrrolidin-2-yl)Methanol is an attractive candidate for various chemical and biological applications. It may be used in the development of new materials, sensors, or as a component in biological assays where its unique properties can be leveraged for specific analytical or diagnostic purposes.

InChI:InChI=1S/C21H15F12NO/c22-18(23,24)12-4-10(5-13(8-12)19(25,26)27)17(35,16-2-1-3-34-16)11-6-14(20(28,29)30)9-15(7-11)21(31,32)33/h4-9,16,34-35H,1-3H2/t16-/m0/s1

Upstream product

• 1146629-85-7 (7aR)-1,1-bis(3,5-bis(trifluoromethyl)phenyl)tetrahydropyrrolo[1,2-c]oxazol-3(1H)-one 
• 185246-66-6 1-ethyl methyl (2R)-pyrrolidine-1,2-dicarboxylate 
• 328-70-1 3,6-bis(trifluoromethyl)bromobenzene 
• 344-25-2 D-Prolin 

Downstream Products

• 908303-26-4 (R)-(-)-α,α-bis[3,5-bis(trifluoromethyl)phenyl]-2-pyrrolidinemethanoltrimethylsilyl ether 
• 1146629-74-4 (R)-α,α-bis[3,5-bis(trifluoromethyl)phenyl]-2-pyrrolidinemethanol (tert-butyl)dimethylsilyl ether 
• 1061307-56-9 (2R)-2-(bis[3,5-bis(trifluoromethyl)phenyl][(triethylsilyl)oxy]methyl)pyrrolidine 

Relevant academic research and scientific papers

Enantioselective Total Synthesis of (+)-Heilonine

Chemical transformations that rapidly and efficiently construct a high level of molecular complexity in a single step are perhaps the most valuable in total synthesis. Among such transformations is the transition metal catalyzed [2 + 2 + 2] cycloisomerization reaction, which forges three new C-C bonds and one or more rings in a single synthetic operation. We report here a strategy that leverages this transformation to open de novo access to the Veratrum family of alkaloids. The highly convergent approach described herein includes (i) the enantioselective synthesis of a diyne fragment containing the steroidal A/B rings, (ii) the asymmetric synthesis of a propargyl-substituted piperidinone (F ring) unit, (iii) the high-yielding union of the above fragments, and (iv) the intramolecular [2 + 2 + 2] cycloisomerization reaction of the resulting carbon framework to construct in a single step the remaining three rings (C/D/E) of the hexacyclic cevanine skeleton. Efficient late-stage maneuvers culminated in the first total synthesis of heilonine (1), achieved in 21 steps starting from ethyl vinyl ketone.

PROCESSES FOR PREPARING JAK INHIBITORS AND RELATED INTERMEDIATE COMPOUNDS

The present invention is related to processes for preparing chiral substituted pyrazolyl pyrrolo[2,3-d]pyrimidines of Formula III, and related synthetic intermediate compounds. The chiral substituted pyrazolyl pyrrolo[2,3-d]pyrimidines are useful as inhibitors of the Janus Kinase family of protein tyrosine kinases (JAKs) for treatment of inflammatory diseases, myeloproliferative disorders, and other diseases.

Enantioselective synthesis of janus kinase inhibitor INCB018424 via an organocatalytic aza-michael reaction

An enantioselective synthesis of INCB018424 via organocatalytic asymmetric aza-Michael addition of pyrazoles (16 or 20) to (E)-3- cyclopentylacrylaldehyde (23) using diarylprolinol silyl ether as the catalyst was developed. Michael adducts (R)-24 and (R)-27 were isolated in good yield and high ee and were readily converted to INCB018424.