118971-03-2

Basic information

• Product Name: (S)-2-(Methoxydiphenylmethyl)pyrrolidine
• Synonyms: (S)-2-(Methoxydiphenylmethyl)pyrrolidine;(S)-2-(MethoxydiphenylMethyl)pyrrolidine 95% (HPLC);(2S)-2-[Diphenyl(methoxy)methyl]pyrrolidine;(2S)-2-[Diphenyl(methoxy)methyl]tetrahydropyrrole;-2-(Methoxydiphenylmethyl)
• CAS NO: 118971-03-2
• Molecular Formula: C₁₈H₂₁NO
• Molecular Weight: 267.36544
• Product Categories: Asymmetric Synthesis;Chiral Catalysts, Ligands, and Reagents;Proline-Based Organocatalysts
• Mol File: 118971-03-2.mol

Chemical Properties

• Boiling Point: 368.677 °C at 760 mmHg
• Flash Point: 157.824 °C
• Appearance: white to beige crystals or crystalline powder
• Density: 1.07 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.564
• Storage Temp.: 2-8°C
• PKA: 10.09±0.10(Predicted)
• CAS DataBase Reference: (S)-2-(Methoxydiphenylmethyl)pyrrolidine(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-(Methoxydiphenylmethyl)pyrrolidine(118971-03-2)
• EPA Substance Registry System: (S)-2-(Methoxydiphenylmethyl)pyrrolidine(118971-03-2)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• WGK Germany: 3
• Hazardous Substances Data: 118971-03-2(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
(S)-2-(Methoxydiphenylmethyl)pyrrolidine is used as a catalyst for the enantioselective synthesis of ketones via intermolecular asymmetric Michael addition of aldehydes to nonactivated enones. This application is significant in the production of chiral compounds, which are essential in the pharmaceutical industry for the development of drugs with specific biological activities.
Used in Pharmaceutical Industry:
(S)-2-(Methoxydiphenylmethyl)pyrrolidine is used as a catalyst for the synthesis of stereoselective chiral bipyrazolidin-3-one derivatives by dipolar cycloaddition reaction of azomethine imines with α, β-unsaturated aldehydes. These chiral derivatives are valuable in the development of new drugs with improved efficacy and selectivity.
Used in Organic Chemistry Research:
(S)-2-(Methoxydiphenylmethyl)pyrrolidine is used as a catalyst for the synthesis of enantioenriched spiro nitrogen heterocycles via asymmetric nucleophilic epoxidation of α-ylideneoxindole esters. The development of such heterocycles is crucial for the creation of novel compounds with potential applications in various fields, including pharmaceuticals and materials science.
Used in Asymmetric Synthesis of Alcohols:
(S)-2-(Methoxydiphenylmethyl)pyrrolidine is used as a catalyst for the asymmetric addition of Et2Zn to various aldehydes, leading to the formation of optically active secondary alcohols. These alcohols are important building blocks in the synthesis of complex organic molecules and have applications in the production of pharmaceuticals, agrochemicals, and other specialty chemicals.

InChI:InChI=1/C18H21NO/c1-20-18(17-13-8-14-19-17,15-9-4-2-5-10-15)16-11-6-3-7-12-16/h2-7,9-12,17,19H,8,13-14H2,1H3/t17-/m0/s1

Upstream product

• 118970-99-3 (S)-(-)-1-benzyl-2-(1-methoxy-1,1-diphenylmethyl)-pyrrolidine 
• 5817-26-5 ethyl (2S)-pyrrolidine-2-carboxylate 
• 147-85-3 L-proline 
• 118970-95-9 (S)-1-benzyl-2-(hydroxydiphenylmethyl)pyrrolidine 
• 955-40-8 N-benzyl-L-proline ethyl ester 

Downstream Products

• 199934-17-3 (S)-2-(Methoxy-diphenyl-methyl)-1-((E)-2-nitro-propenyl)-pyrrolidine 
• 118535-63-0 (S)-(-)-1-amino-2-(1'-methoxy-1',1'-diphenylmethyl)pyrrolidine 
• 1329994-59-3 (S)-N-dichlorothiophosphoryl-2-(methoxydiphenylmethyl)pyrrolidine 
• 1296306-99-4 C₂₂H₂₇NO 
• 1296306-94-9 C₂₃H₂₉NO 
• 1296307-00-0 C₂₀H₂₃NO 
• 1296306-95-0 C₂₁H₂₅NO 
• 163814-41-3 (S)-2-methoxydiphenylmethyl-1-(2-nitrovinyl)pyrrolidine 
• 118535-72-1 1-nitroso-2-(1'-methoxy-1',1'-diphenyl)pyrrolidine 

Relevant articles and documents

Fluorinated chiral secondary amines as catalysts for epoxidation of olefins with oxone

(Chemical Equation Presented) We have synthesized a series of chiral cyclic secondary amines having different substitution patterns and have screened them as catalysts for the asymmetric epoxidation of olefins using Oxone. The highest enantiomeric excess (61%) occurred for the epoxidation of 1-phenylcyclohexene catalyzed by a secondary amine bearing a fluorine atom at the β-position relative to the amino center. Our experimental results provide further support to the notion that the amine plays a dual role - as a phase transfer catalyst and an Oxone activator - in these epoxidation reactions. The slightly acidic reaction conditions we employed in this work obviate the need to preform ammonium salts, which are the actual catalysts that mediate the epoxidations.

LARGE SCALE PREPARATION OF VERSATILE CHIRAL AUXILIARIES DERIVED FROM (S)-PROLINE

The synthesis of a variety of enantiomerically pure chiral auxiliaries based on (S)-proline and bearing sterically demanding side chains at the pyrrolidine moiety, such as the secondary amines (S)-3,5 and 7 and the hydrazines (S)-6, is described on a molar scale.As key step, the Grignard or RLi addition to the N-benzylated proline ester (S)-1 is used.