914299-82-4

Basic information

• Product Name: (S)-2-O-TOLYLPYRROLIDINE
• Synonyms: (S)-2-O-TOLYLPYRROLIDINE;(2S)-2-(2-METHYLPHENYL)PYRROLIDINE
• CAS NO: 914299-82-4
• Molecular Formula: C11H15N
• Molecular Weight: 161.24
• Mol File: 914299-82-4.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (S)-2-O-TOLYLPYRROLIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-O-TOLYLPYRROLIDINE(914299-82-4)
• EPA Substance Registry System: (S)-2-O-TOLYLPYRROLIDINE(914299-82-4)

Safety Data

• Hazardous Substances Data: 914299-82-4(Hazardous Substances Data)

Usage

Description

(S)-2-O-TOLYLPYRROLIDINE, with the molecular formula C11H15N, is a pyrrolidine derivative featuring a tolyl group attached to the second carbon of the pyrrolidine ring. This chiral compound is widely recognized for its utility in organic synthesis, particularly in the production of pharmaceuticals and agrochemicals.

Uses

Used in Pharmaceutical Industry:
(S)-2-O-TOLYLPYRROLIDINE is used as a chiral building block for the synthesis of various pharmaceuticals, leveraging its ability to impart chirality to molecules. This property is crucial in creating enantiomerically pure compounds, which are essential for the development of effective and safe drugs.
Used in Agrochemical Industry:
In the agrochemical sector, (S)-2-O-TOLYLPYRROLIDINE serves as a chiral building block, contributing to the development of enantiomerically pure agrochemicals. This ensures targeted effects on pests and weeds while minimizing potential side effects on non-target organisms and the environment.
Used in Asymmetric Catalysis:
(S)-2-O-TOLYLPYRROLIDINE is utilized as a chiral ligand in asymmetric catalysis, a technique that allows for the selective formation of one enantiomer over another. This application is vital for producing enantiomerically pure compounds with specific biological activities, enhancing the efficiency and selectivity of chemical reactions in both pharmaceutical and chemical industries.

Upstream product

• 123-75-1 pyrrolidine 
• 6699-93-0 (2-methylphenyl)lithium 
• 95-46-5 2-methylphenyl bromide 
• 121091-12-1 3,4-dihydro-5-(2-methylphenyl)-2H-pyrrole 
• 87-24-1 ethyl 2-methylbenzoate 
• 118-90-1 ortho-methylbenzoic acid 
• 529-20-4 2-methylphenyl aldehyde 

Relevant articles and documents

Zinc-Catalyzed Asymmetric Hydrosilylation of Cyclic Imines: Synthesis of Chiral 2-Aryl-Substituted Pyrrolidines as Pharmaceutical Building Blocks

The first successful enantioselective hydrosilylation of cyclic imines promoted by a chiral zinc complex is reported. In situ generated zinc-ProPhenol complex with silane afforded pharmaceutically relevant enantioenriched 2-aryl-substituted pyrrolidines in high yields and with excellent enantioselectivities (up to 99% ee). The synthetic utility of presented methodology is demonstrated in an efficient synthesis of the corresponding chiral cyclic amines, being pharmaceutical drug precursors to the Aticaprant and Larotrectinib. (Figure presented.).

CHIRAL CATALYST AND METHOD FOR ASYMMETRIC REDUCTION OF AN IMINE

The present disclosure discusses (i) a compound having a chemical formula according to Formula (I), or its enantiomer; and (ii) a compound that is reactive with a hydride to produce a compound having a chemical formula according to Formula (I), or its enantiomer. Formula (I) is: Formula (I) where R1 and R2 are H, optionally substituted C1-C3 alkyl, or linked together to form an optionally substituted C3 or C4 alkyl group; R3 and R3' are H; R4 and R4' are the same, and are optionally substituted C1-C6 alkyl; and R5 and R5' are the same, and are optionally substituted aryl or heteroaryl. In some examples, R4 and R5 are linked, and R4' and R5' are linked, where both linking groups are the same. The present disclosure also discusses methods of asymmetric reduction of an imine, and methods of forming the catalysts and pre-catalysts.

Direct α-C-H bond functionalization of unprotected cyclic amines

Cyclic amines are ubiquitous core structures of bioactive natural products and pharmaceutical drugs. Although the site-selective abstraction of C-H bonds is an attractive strategy for preparing valuable functionalized amines from their readily available parent heterocycles, this approach has largely been limited to substrates that require protection of the amine nitrogen atom. In addition, most methods rely on transition metals and are incompatible with the presence of amine N-H bonds. Here we introduce a protecting-group-free approach for the α-functionalization of cyclic secondary amines. An operationally simple one-pot procedure generates products via a process that involves intermolecular hydride transfer to generate an imine intermediate that is subsequently captured by a nucleophile, such as an alkyl or aryl lithium compound. Reactions are regioselective and stereospecific and enable the rapid preparation of bioactive amines, as exemplified by the facile synthesis of anabasine and (-)-solenopsin A.