4787-76-2

Usage

Uses

Used in Research Applications:
Pyrrolidine, 1-(2-methoxyphenyl)is used as a research chemical for studying the effects of substituted amphetamines on the central nervous system. Its interaction with dopamine and norepinephrine receptors provides insights into the mechanisms of action of stimulant drugs and their potential for abuse.
Used in Pharmaceutical Development:
Pyrrolidine, 1-(2-methoxyphenyl)can be used in the development of new pharmaceuticals targeting the dopamine and norepinephrine receptors. Understanding its effects and mechanisms of action may aid in the creation of safer and more effective medications for the treatment of various conditions.
Used in Forensic Toxicology:
Pyrrolidine, 1-(2-methoxyphenyl)is used in forensic toxicology for the identification and analysis of designer drugs in biological samples. Its detection in cases of drug abuse or overdose can provide valuable information for legal and medical purposes.
Used in Drug Control and Regulation:
Pyrrolidine, 1-(2-methoxyphenyl)is used in the development and enforcement of drug control policies and regulations. Its classification as a controlled substance helps to prevent its abuse and distribution, protecting public health and safety.

Upstream product

• 110-52-1 1,4-dibromo-butane 
• 90-04-0 2-methoxy-phenylamine 
• 123-75-1 pyrrolidine 
• 91-16-7 1,2-dimethoxybenzene 
• 201230-82-2 carbon monoxide 
• 15258-47-6 2-methoxy-N-allylaniline 
• 638-37-9 butanedial 
• 766-51-8 2-Chloroanisole 
• 578-57-4 2-bromoanisole 
• 529-28-2 4-iodoanisol 
• 3425-23-8 2-methoxybenzenediazonium chloride 
• 23196-06-7 1-(2-methoxyphenyl)pyrrolidin-2-one 
• 2393-23-9 4-methoxy-benzylamine 
• 629-03-8 1 ,6-dibromohexane 

Downstream Products

• 4787-77-3 2-(pyrrolidin-1-yl)phenol 
• 109366-12-3 1-(2-dimethylcarbamoyloxy-phenyl)-1-methyl-pyrrolidinium; iodide 
• 101264-86-2 dimethyl-carbamic acid-(2-pyrrolidino-phenyl ester) 

Relevant academic research and scientific papers

Dehydrogenation/(3+2) Cycloaddition of Saturated Aza-Heterocycles via Merging Organic Photoredox and Lewis Acid Catalysis

Herein, we report a photoinduced dehydrogenation/(3+2) cycloaddition reaction by merging organic photoredox and Lewis acid catalysis, providing a straightforward and efficient approach for directly installing a benzofuran skeleton on the saturated aza-heterocycles. In this protocol, we also describe a novel organic photocatalyst (t-Bu-DCQ) with the advantages of a wider redox potential, easy synthesis, and a low price. Furthermore, the stepwise activation mechanism of dual C(sp3)-H bonds was demonstrated by a series of experimental and computational studies.

Organic photoredox catalytic α-C(sp3)-H phosphorylation of saturated: Aza -heterocycles

A metal-free C(sp3)-H phosphorylation of saturated aza-heterocycles via the merger of organic photoredox and Br?nsted acid catalyses was established under mild conditions. This protocol provided straightforward and economic access to a variety of valuable α-phosphoryl cyclic amines by using commercially available diarylphosphine oxide reagents. In addition, the D-A fluorescent molecule DCQ was used for the first time as a photocatalyst and exhibited an excellent photoredox catalytic efficiency in this transformation. A series of mechanistic experiments and DFT calculations demonstrated that this transformation underwent a sequential visible light photoredox catalytic oxidation/nucleophilic addition process.

Dialkylterphenyl Phosphine-Based Palladium Precatalysts for Efficient Aryl Amination of N-Nucleophiles

A series of 2-aminobiphenyl palladacycles supported by dialkylterphenyl phosphines, PR2Ar′ (R=Me, Et, iPr, Cyp (cyclopentyl), Ar′=ArDipp2, ArXyl2f, Dipp (2,6-C6H3-(2,6-C6H3-(CHMe2)2)2), Xyl=xylyl) have been prepared and structurally characterized. Neutral palladacycles were obtained with less bulky terphenyl phosphines (i.e., Me and Et substituents) whereas the largest phosphines provided cationic palladacycles in which the phosphines adopted a bidentate hemilabile k1-P,η1-Carene coordination mode. The influence of the ligand structure on the catalytic performance of these Pd precatalysts was evaluated in aryl amination reactions. Cationic complexes bearing the phosphines PiPr2ArXyl2 and PCyp2ArXyl2 were the most active of the series. These precatalysts have demonstrated a high versatility and efficiency in the coupling of a variety of nitrogen nucleophiles, including secondary amines, alkyl amines, anilines, and indoles, with electronically deactivated and ortho-substituted aryl chlorides at low catalyst loadings (0.25–0.75 mol % Pd) and without excess ligand.

Tropane alkaloid compounds and method of manufacturing using sequential oxidation reactions

The present invention relates to a tropane alkaloid compound sequentially using an oxidative Mannich ring reaction and a method for producing the same. The present invention provides a tropane alkaloid compound having a structure of chemical formula 1 in

Methyl-α-d-glucopyranoside as Green Ligand for Selective Copper-Catalyzed N-Arylation

In the selective N-arylation of amines or azoles with aryl halidesa-, methyl-α-d-glucopyranoside (MG) was found to function as a green ligand of copper powder. In addition, nitrogen heterocyclic amine compounds can also undergo the N-arylation coupling with heterocyclic aryl chlorides. This process allows access to a variety of aromatic amines and aryl azoles under mild reaction conditions, has good tolerance, and proceeds in moderate to high yield.

Cu(II)-catalyzed C-N coupling of (hetero)aryl halides and N-Nucleophiles promoted by α-benzoin oxime

We first reported the new application of a translate metal chelating ligand α-benzoin oxime for improving Cu-catalyzed C-N coupling reactions. The system could catalyse coupling reactions of (hetero)aryl halides with a wide of nucleophiles (e.g., azoles, piperidine, pyrrolidine and amino acids) in moderate to excellent yields. The protocol allows rapid access to the most common scaαolds found in FDA-approved pharmaceuticals.

Utilization of Cyclic Amides as Masked Aldehyde Equivalents in Reductive Amination Reactions

An operationally simple protocol has been discovered that couples primary or secondary amines with N-aryl-substituted lactams to deliver differentiated diamines in moderate to high yields. The process allows for the partial reduction of a lactam in the presence of Cp2ZrHCl (Schwartz's reagent), followed by a reductive amination between the resulting hemiaminal and primary or secondary amine. These reactions can be telescoped in a one-pot fashion to significantly simplify the operation. The scope of amines and substituted lactams of various ring sizes was demonstrated through the formation of a range of differentiated diamine products. Furthermore, this methodology was expanded to include N-aryl pyrrolidinone substrates with an enantiopure ester group at the 5-position, and α-amino piperidinones were prepared with complete retention of stereochemical information. The development of this chemistry has enabled the consideration of lactams as useful synthons.

Transition-Metal-Free Selective C?H Benzylation of Tertiary Arylamines by a Dearomatization-Aromatization Sequence

Due to the significance of hybrid systems in drug discovery, there is an urgent need to assemble multiple biologically active ingredients into a single molecule. Here, we report a general transition-metal-free selective C?H benzylation of tertiary arylamines in good to excellent yields with a broad substrate scope and high functional-group tolerance under mild conditions. Besides arylamines, some other benzene derivatives also readily furnished the corresponding diaryl methane derivatives with this protocol. A series of control experiments and theoretical calculations indicated that this transition-metal-free reaction is a dearomatization-aromatization process.

Construction of 8-Azabicyclo[3.2.1]octanes via Sequential DDQ-Mediated Oxidative Mannich Reactions of N-Aryl Pyrrolidines

A concise synthesis of 8-azabicyclo[3.2.1]octanes via sequential oxidative Mannich reactions is described. This approach involves an intermolecular oxidative Mannich coupling reaction between N-aryl pyrrolidines with TMS enol ether and a subsequent intramolecular oxidative Mannich cyclization of the corresponding silyl enol ether. DDQ is used as a key oxidant for both reactions.

Discovery of N-(Naphthalen-1-yl)-N′-alkyl Oxalamide Ligands Enables Cu-Catalyzed Aryl Amination with High Turnovers

A class of N-(naphthalen-1-yl)-N′-alkyl oxalamides have been proven to be powerful ligands, making a coupling reaction of (hetero)aryl iodides with primary amines proceed at 50 °C with only 0.01 mol % of Cu2O and ligand as well as a coupling reaction of (hetero)aryl bromides with primary amines and ammonia at 80 °C with only 0.1 mol % of Cu2O and ligand. A wide range of coupling partners work well under these conditions, thereby providing an easy to operate method for preparing (hetero)aryl amines.