848821-76-1

Basic information

• Product Name: (S)-2-{Bis[3,5-bis(trifluoromethyl)phenyl]hydroxymethyl}pyrrolidine
• Synonyms: Bis(3,5-bis(trifluoroMethyl)phenyl)(pyrrolidin-2-yl)Methanol;2-PyrrolidineMethanol, a,a-bis[3,5-bis(trifluoroMethyl)phenyl]-, (2S)-;(S)-α,α-Bis[3,5-bis(trifluoroMethyl)phenyl]-2-pyrrolidineMethanol >=99.0%;(S)-Bis(3,5-bis(trifluoromethyl)phenyl)(pyrrolidin-2-yl)methanol;(S)-alpha,alpha-Bis[3,5-bis(trifluoromethyl)phenyl]-2-pyrrolidinemethanol >=99.0%;(S)-α,α-Bis[3,5-bis(trifluoromethyl)phenyl]-2- pyrrolidinemethanol,99%e.e.;(S)-2-{Bis[3,5-bis(trifluoromethyl)phenyl]hydroxymethyl}pyrrolidine;(S)-α,α-Bis[3,5-bis(trifluoromethyl)phenyl]-2-pyrrolidinemethanol
• CAS NO: 848821-76-1
• Molecular Formula: C₂₁H₁₅F₁₂NO
• Molecular Weight: 525.33
• Mol File: 848821-76-1.mol
• Article Data: 6

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: (S)-2-{Bis[3,5-bis(trifluoromethyl)phenyl]hydroxymethyl}pyrrolidine(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-{Bis[3,5-bis(trifluoromethyl)phenyl]hydroxymethyl}pyrrolidine(848821-76-1)
• EPA Substance Registry System: (S)-2-{Bis[3,5-bis(trifluoromethyl)phenyl]hydroxymethyl}pyrrolidine(848821-76-1)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 848821-76-1(Hazardous Substances Data)

Usage

General Description

(S)-2-{Bis[3,5-bis(trifluoromethyl)phenyl]hydroxymethyl}pyrrolidine is a chemical compound with the molecular formula C23H21F12NO. It is a pyrrolidine derivative that contains two trifluoromethylphenyl groups and a hydroxymethyl group. (S)-2-{Bis[3,5-bis(trifluoromethyl)phenyl]hydroxymethyl}pyrrolidine has potential applications in the field of medicinal chemistry as it may exhibit pharmacological activity due to its unique structure. The presence of the trifluoromethyl groups can enhance the compound's lipophilicity and metabolic stability, making it a potential candidate for drug development. Further research is needed to fully understand the pharmacological properties and potential uses of this compound.

Upstream product

• 112981-69-8 3,5-bis(trifluoromethyl)phenylmagnesium bromide 
• 45736-33-2 (S)-proline-N-carboxyanhydride 
• 147-85-3 L-proline 
• 845965-28-8 (S)-1,1-bis(3,5-bis(trifluoromethyl)phenyl)tetrahydro-1H,3H-pyrrolo[1,2-c]oxazol-3-one 
• 1187560-71-9 2-[bis(3,5-bis(trifluoromethyl)phenyl)hydroxymethyl]pyrrolidine-1-carboxylic acid ethyl ester 
• 113304-84-0 N-benzyl-(S)-proline methyl ester 
• 1206166-84-8 (S)-(1-benzylpyrrolidin-2-yl)bis(3,5-bis(trifluoromethyl)phenyl)methanol 
• 2577-48-2 methyl (2S)-pyrrolidine carboxylate 

Downstream Products

• 848821-61-4 (S)-2-{bis[3,5-bis(trifluoromethyl)phenyl][(trimethylsilanyl)oxy]methyl}pyrrolidine 
• 951008-61-0 C₂₇H₁₇N₂O₂ClF₁₂ 
• 951008-65-4 {(2S)-2-{bis[3,5-bis(trifluoromethyl)phenyl]hydroxymethyl}-1-pyrrolidinyl}[4-(1-pyrrolidinyl)-3-pyridinyl]methanone 
• 1296307-08-8 C₂₄H₁₉F₁₂NO 
• 1296306-93-8 C₂₄H₁₉F₁₂NO 
• 1296307-07-7 C₂₆H₂₃F₁₂NO 
• 1296306-92-7 C₂₆H₂₃F₁₂NO 
• 1357262-39-5 (S)-2-(bis(3,5-bis(trifluoromethyl)phenyl)((methyldiphenylsilyl)oxy)methyl)pyrrolidine 
• 1536481-20-5 (2R,3R)-4-(tert-butoxy)-1,3-dihydroxy-4-oxobutan-2-yl 2,6-dimethylbenzoate 
• 1536481-31-8 C₃₈H₃₅F₁₂NO₆ 

Relevant articles and documents

London Dispersion Interactions Rather than Steric Hindrance Determine the Enantioselectivity of the Corey–Bakshi–Shibata Reduction

The well-known Corey–Bakshi–Shibata (CBS) reduction is a powerful method for the asymmetric synthesis of alcohols from prochiral ketones, often featuring high yields and excellent selectivities. While steric repulsion has been regarded as the key director of the observed high enantioselectivity for many years, we show that London dispersion (LD) interactions are at least as important for enantiodiscrimination. We exemplify this through a combination of detailed computational and experimental studies for a series of modified CBS catalysts equipped with dispersion energy donors (DEDs) in the catalysts and the substrates. Our results demonstrate that attractive LD interactions between the catalyst and the substrate, rather than steric repulsion, determine the selectivity. As a key outcome of our study, we were able to improve the catalyst design for some challenging CBS reductions.

Organocatalytic enantioselective α-hydroxymethylation of aldehydes: Mechanistic aspects and optimization

Further studies of the direct enantioselective α-hydroxymethylation of aldehydes employing the α,α-diarylprolinol trimethylsilyl ether class of organocatalysts are described. This process has proven efficient for access to β-hydroxycarboxylic acids and δ-hydroxy-α,β-unsaturated esters from aldehydes in generally good yields, excellent enantioselectivity, and compatibility with a broad range of functional groups in the aldehyde. The goal of these studies was to identify the critical reaction variables that influence the yield and enantioselectivity of the α-hydroxymethylation process such as catalyst structure, pH of the medium, purity of the reactants and reagents particularly with respect to the presence of acidic impurities, and the nature of the buffer, along with the standard variables including solvent, time, temperature and mixing efficiency. The previously identified intermediate lactol has been further characterized and its reactivity examined. These studies have led to identification of the most critical variables translating directly into improved substrate scope, reproducibility, enantioselectivity, and yields.

Nonenzymatic acylative kinetic resolution of Baylis-Hillman adducts

(Chemical Equation Presented) The first efficient nonenzymatic acylative kinetic resolution of Baylis-Hillman adducts is reported. Chiral pyridine catalyst 1a and an optimized analogue 1e are capable of promoting the synthetically useful enantioselective