948595-00-4

Basic information

• Product Name: (R)-bis(3,5-bis(trifluoroMethyl)phenyl)(pyrrolidin-2-yl)Methanol
• Synonyms: (R)-bis(3,5-bis(trifluoroMethyl)phenyl)(pyrrolidin-2-yl)Methanol;2-PyrrolidineMethanol, a,a-bis[3,5-bis(trifluoroMethyl)phenyl]-, (2R)-;(R)-α,α-Bis[3,5-bis(trifluoroMethyl)phenyl]-2-pyrrolidineMethanol >=99.0%;(R)-alpha,alpha-Bis[3,5-bis(trifluoromethyl)phenyl]-2-pyrrolidinemethanol >=99.0%;(R)-bis(3,5-bis(trifluoroMethyl)phenyl)(pyrrolidin-2-yl)Methano;(2R)-alpha,alpha-Bis[3,5-bis(trifluoromethyl)phenyl]-2-pyrrolidinemethanol;(R)-α,α-Bis[3,5-bis(trifluoromethyl)phenyl]-2- pyrrolidinemethanol,99%e.e.
• CAS NO: 948595-00-4
• Molecular Formula: C₂₁H₁₅F₁₂NO
• Molecular Weight: 525.3307384
• Mol File: 948595-00-4.mol
• Article Data: 3

Chemical Properties

• Melting Point: 113-117°C
• Boiling Point: 391.8±42.0 °C(Predicted)
• Appearance: /
• Density: 1.465±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 12.26±0.29(Predicted)
• CAS DataBase Reference: (R)-bis(3,5-bis(trifluoroMethyl)phenyl)(pyrrolidin-2-yl)Methanol(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-bis(3,5-bis(trifluoroMethyl)phenyl)(pyrrolidin-2-yl)Methanol(948595-00-4)
• EPA Substance Registry System: (R)-bis(3,5-bis(trifluoroMethyl)phenyl)(pyrrolidin-2-yl)Methanol(948595-00-4)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 948595-00-4(Hazardous Substances Data)

Usage

General Description

(R)-bis(3,5-bis(trifluoroMethyl)phenyl)(pyrrolidin-2-yl)Methanol is a chemical compound with the molecular formula C25H26F12NO and a molecular weight of 571.47 g/mol. It is a chiral compound with a pyrrolidinylmethanol core and two 3,5-bis(trifluoromethyl)phenyl groups. (R)-bis(3,5-bis(trifluoroMethyl)phenyl)(pyrrolidin-2-yl)Methanol is commonly used as a reagent in organic synthesis and pharmaceutical research, particularly in the development of chiral catalysts and ligands. Its chiral nature makes it a valuable tool in asymmetric synthesis, where selectivity and stereochemistry are crucial. Additionally, its potentially low toxicity and high stability make it an attractive candidate for use in various chemical and biological applications.

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 
• 344-25-2 D-Prolin 
• 328-70-1 3,6-bis(trifluoromethyl)bromobenzene 
• 185246-66-6 1-ethyl methyl (2R)-pyrrolidine-1,2-dicarboxylate 

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 articles and documents

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.

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.