131180-63-7

Basic information

• Product Name: (S)-(-)-2-[Bis(3,5-dimethylphenyl)hydroxymethyl]pyrrolidine
• Synonyms: (S)-(-)-2-[Bis(3,5-dimethylphenyl)hydroxymethyl]pyrrolidine;(S)-α,α-Bis(3,5-dimethylphenyl)-2-pyrrolidinemethanol;(S)-α,α-Bis(3,5-diMethylphenyl)-2-pyrrolidineMethanol >=99% (HPLC);(S)-alpha,alpha-Bis(3,5-dimethylphenyl)-2-pyrrolidinemethanol >=99% (HPLC);(S)-α,α-Bis(3,5-dimethylphenyl)-2-pyrrolidinemethanol,99%e.e.;(S)-Bis(3,5-dimethylphenyl)(pyrrolidin-2-yl)methanol
• CAS NO: 131180-63-7
• Molecular Formula: C₂₁H₂₇NO
• Molecular Weight: 309.45
• Mol File: 131180-63-7.mol
• Article Data: 7

Chemical Properties

• Melting Point: 98-101 °C
• Boiling Point: 488.2±35.0 °C(Predicted)
• Appearance: /
• Density: 1.068±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 13.70±0.29(Predicted)
• CAS DataBase Reference: (S)-(-)-2-[Bis(3,5-dimethylphenyl)hydroxymethyl]pyrrolidine(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(-)-2-[Bis(3,5-dimethylphenyl)hydroxymethyl]pyrrolidine(131180-63-7)
• EPA Substance Registry System: (S)-(-)-2-[Bis(3,5-dimethylphenyl)hydroxymethyl]pyrrolidine(131180-63-7)

Safety Data

• Hazard Codes: Xn,N
• Statements: 22-50/53
• Safety Statements: 60-61
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• Hazardous Substances Data: 131180-63-7(Hazardous Substances Data)

Usage

Uses

(S)-α,α-Bis(3,5-dimethylphenyl)-2-pyrrolidinemethanol can be used as: A chiral organocatalyst in the preparation of α-[(phenyl)methyl]thio]alkanal derivatives using aldehydes as starting materials and [(phenyl)methyl]thio]triazole as a sulfur electrophile. A catalyst in the preparation of chiral bipyrazolidin-3-one derivatives by cycloadditions of azomethine imines with α,β-unsaturated aldehydes.

Upstream product

• 34696-73-6 3,5-dimethyphenylmagnesium bromide 
• 45736-33-2 (S)-proline-N-carboxyanhydride 
• 147-85-3 L-proline 
• 556-96-7 5-bromo-1,3-xylene 
• 955-40-8 N-benzyl-L-proline ethyl ester 

Downstream Products

• 1103893-48-6 (S)-(2-(bis(3,3-dimethylphenyl)(hydroxy)methyl)pyrrolidin-1-yl)(pyridin-2-yl)methanone 
• 1259027-78-5 (S)-2-((tert-butyldimethylsilyloxy)bis(3,5-dimethylphenyl)methyl)pyrrolidine 
• 1350706-59-0 CHF₃O₃S*C₃₁H₃₂BNO 
• 1401455-91-1 C₂HF₆NO₄S₂*C₂₇H₃₀BNO 
• 1296307-05-5 C₂₆H₃₅NO 
• 1296306-88-1 C₂₆H₃₅NO 
• 1296307-06-6 C₂₄H₃₁NO 
• 1296306-89-2 C₂₄H₃₁NO 

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.

Enantioselective Intermolecular [2+2] Photocycloaddition Reaction of Cyclic Enones and Its Application in a Synthesis of (-)-Grandisol

The intermolecular [2+2] photocycloaddition of typical cyclic α,β-unsaturated enones, such as 2-cyclohexenone, with olefins was performed in moderate to good yields (42-82%) and with high enantioselectivity (82%-96% ee). An unusual substitution pattern at the chiral oxazaborolidine-AlBr3 Lewis acid complex that promotes the reaction was found to be crucial for the success of the reaction. The method was applied to the enantioselective synthesis of the monoterpene (-)-grandisol, which could be accomplished in six steps and with an overall yield of 13% starting from 3-methyl-2-cyclohexenone.

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