1217847-41-0

Basic information

• Product Name: (2S)-2-(4-Methylphenyl)pyrrolidine
• Synonyms: (2S)-2-(4-Methylphenyl)pyrrolidine
• CAS NO: 1217847-41-0
• Molecular Weight: 161.247
• Mol File: 1217847-41-0.mol

Chemical Properties

• CAS DataBase Reference: (2S)-2-(4-Methylphenyl)pyrrolidine(CAS DataBase Reference)
• NIST Chemistry Reference: (2S)-2-(4-Methylphenyl)pyrrolidine(1217847-41-0)
• EPA Substance Registry System: (2S)-2-(4-Methylphenyl)pyrrolidine(1217847-41-0)

Safety Data

• Hazardous Substances Data: 1217847-41-0(Hazardous Substances Data)

Usage

Uses

Used in Medicinal Chemistry:
(2S)-2-(4-Methylphenyl)pyrrolidine is utilized as a key intermediate in the synthesis of various pharmaceutical compounds due to its distinctive structure and potential biological activities. Its hydrophobic nature, stemming from the methyl group on the phenyl ring, allows for specific interactions with target molecules, making it a valuable component in drug design and development.
Further research and studies are ongoing to explore the pharmacological and therapeutic properties of (2S)-2-(4-Methylphenyl)pyrrolidine, with the aim of identifying its potential applications in treating various diseases and conditions. Its chiral nature also opens up possibilities for the development of enantiomer-specific drugs, which can have different effects and potencies, further expanding its utility in the field of medicinal chemistry.

Upstream product

• 22217-77-2 5-(p-tolyl)-3,4-dihydro-2H-pyrrole 
• 38425-26-2 4-chloro-1-(4-methylphenyl)butan-1-one 
• 1207729-68-7 (S)-1-((S)-2-methyl-propane-2-sulfinyl)-2-(4-methylphenyl)-pyrrolidine 
• 1227798-67-5 C₁₅H₂₂ClNOS 
• 1227798-72-2 C₁₁H₁₅N*ClH 

Downstream Products

• 1452523-61-3 C₁₈H₁₉NO 

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.).

Enantioselective Synthesis of 2-Substituted Pyrrolidines via Intramolecular Reductive Amination

Catalyzed by the complex generated in situ from iridium and the chiral ferrocene ligand, tert -butyl (4-oxo-4-arylbutyl)carbamate substrates were deprotected and then reductively cyclised to form 2-substituted arylpyrrolidines in a one-pot manner, in which the intramolecular reductive amination was the key step. A range of chiral 2-substituted arylpyrrolidines were synthesised in up to 98percent yield and 92percent ee.

Synthesis of nitrogenated heterocycles by asymmetric transfer hydrogenation of N-(tert-butylsulfinyl)haloimines

Highly optically enriched, protected, nitrogenated heterocycles with different ring sizes have been synthesized by a very efficient methodology consisting of the asymmetric transfer hydrogenation of N-(tert-butylsulfinyl) haloimines followed by treatment with a base to promote an intramolecular nucleophilic substitution process. N-Protected aziridines, pyrrolidines, piperidines, and azepanes bearing aromatic, heteroaromatic, and aliphatic substituents have been obtained in very high yields and diastereomeric ratios up to >99:1. The free heterocycles can be easily obtained by a simple and mild desulfinylation procedure. Both enantiomers of the free heterocycles can be prepared with the same good results by changing the absolute configuration of the sulfur atom of the sulfinyl group.

Asymmetric synthesis of 2-arylpyrrolidines starting from γ-chloro N-(tert-butanesulfinyl)ketimines

The enantioselective reductive cyclization of γ-chloro N-(tert-butanesulfinyl)ketimines towards the short and efficient synthesis of (S)- and (R)-2-arylpyrrolidines (ee >99%) is described for the first time by treatment with LiBEt3H and subsequ