774-91-4

Usage

Uses

Used in Pharmaceutical Industry:
Pyrrolidine, 2-methyl-1-(phenylmethyl)is used as a building block for the synthesis of various pharmaceuticals due to its versatile reactivity, enabling the development of new drugs and medications.
Used in Agrochemical Industry:
Pyrrolidine, 2-methyl-1-(phenylmethyl)is used as a building block for the synthesis of various agrochemicals, contributing to the development of new pesticides and other agricultural chemicals.
Used in Asymmetric Synthesis:
Pyrrolidine, 2-methyl-1-(phenylmethyl)is used as a chiral auxiliary in asymmetric synthesis to create enantiomerically pure compounds, which are important for the production of single-enantiomer drugs and other chiral molecules.
Used in Electronic Materials Development:
Pyrrolidine, 2-methyl-1-(phenylmethyl)has potential applications in the development of novel materials for electronic devices, such as organic semiconductors and other advanced materials.
Used as a Solvent in Chemical Processes:
Pyrrolidine, 2-methyl-1-(phenylmethyl)can be utilized as a solvent in some chemical processes, aiding in the synthesis and processing of various compounds.

Upstream product

• 100-44-7 benzyl chloride 
• 765-38-8 2-methyl-1-pyrrolidine 
• 54436-58-7 N-benzylpent-4-en-1-amine 
• 1119-51-3 bromopentene 
• 100-46-9 benzylamine 
• 56519-58-5 1-benzyl-2-methyl-1-pyrrolinium perchlorate 
• 1430962-42-7 acetophenone N,N-(benzyl(pent-4-en-1-yl)carbamoyl) oxime 
• 1430962-71-2 N-benzyl-N-(pent-4-en-1-yl)-1H-imidazole-1-carboxamide 
• 626-95-9 1,4-Pentanediol 
• 123-76-2 levulinic acid 
• 174500-72-2 Methanesulfonic acid (R)-4-methanesulfonyloxy-1-methyl-butyl ester 
• 56718-04-8 (4R)-pentane-1,4-diol 
• 174500-52-8 (R)-1-(trityloxy)pentan-4-yl acetate 
• 74500-56-4 1,4-pentanediol monotrityl ether 

Downstream Products

• 56519-58-5 1-benzyl-2-methyl-1-pyrrolinium perchlorate 
• 765-38-8 (S)-2-methylpyrrolidine 
• 116614-85-8 ethyl (E)-2-(1-benzylpyrrolidin-2-ylidene)acetate 

Relevant academic research and scientific papers

Design, scope and mechanism of highly active and selective chiral NHC-iridium catalysts for the intramolecular hydroamination of a variety of unactivated aminoalkenes

Chiral, cationic NHC-iridium complexes are introduced as catalysts for the intramolecular hydroamination reaction of unactivated aminoalkenes. The catalysts show high activity in the construction of a range of 5- and 6-membered N-heterocycles, which are accessed in excellent optical purity, with various functional groups being tolerated with this system. A major deactivation pathway is presented and eliminated by using alternative reaction conditions. A detailed experimental and computational study on the reaction mechanism is performed providing valuable insights into the mode of action of the catalytic system and pointing to future modifications to be made for this catalytic platform.

Mild reduction with silanes and reductive amination of levulinic acid using a simple manganese catalyst

A manganese-based catalytic system using the commercially available complex [Mn(CO)5Br] was studied for the selective reduction of levulinic acid (LA) to 2-methyl-tetrahydrofuran (MTHF). We further studied the production of pyrrolidines via its reductive amination using silanes (phenylsilane and tetramethyldisiloxane). The results showed high efficiency and selectivity for this reaction leading to high yields using mild reaction conditions.

On the Superior Activity of In(I) versus In(III) Cations Toward ortho-C-Alkylation of Anilines and Intramolecular Hydroamination of Alkenes

An efficient ortho-C-alkylation of unprotected anilines with a variety of styrenes and alkenes using a univalent cationic indium(I) catalyst is reported. Mechanistic studies revealed that the reaction likely proceeds via a tandem hydroamination/Hofmann-Martius rearrangement. The high compatibility between the cationic indium(I) complex and primary anilines led us to develop an In(I)+-catalyzed hydroamination of alkenes using unprotected primary and secondary alkenylamines. Computations support the catalytic activity of naked In(I)+ ions, with an outer sphere mechanism for the C-N bond formation and a potentially inner sphere protodemetallation.

Noble metal-free upgrading of multi-unsaturated biomass derivatives at room temperature: Silyl species enable reactivity

Biomass derivatives are a class of oxygen-rich organic compounds, which can be selectively upgraded to various value-added molecules by partial or complete hydrogenation over metal catalysts. Here, we show that Cs2CO3, a low-cost commercial chemical, enables the selective reduction of dicarbonyl compounds including bio-derived carboxides to monohydric esters/amides, hydroxylamines or diols with high yields (82-99%) at room temperature using eco-friendly and equivalent hydrosilane as a hydride donor. The in situ formation of silyl ether enables the developed catalytic system to tolerate other unsaturated groups and permits a wide substrate scope with high selectivities. Spectroscopic and computational studies elucidate reaction pathways with an emphasis on the role of endogenous siloxane.

Reductive amination/cyclization of levulinic acid to pyrrolidones: Versus pyrrolidines by switching the catalyst from AlCl3 to RuCl3 under mild conditions

Herein the reductive amination/cyclization of levulinic acid using phenylsilane was presented to selectively produce pyrrolidones versus pyrrolidines under mild conditions by switching the catalyst from AlCl3 to RuCl3. Using AlCl3 as the catalyst, pyrrolidones were solely obtained at room temperature, while RuCl3 as the catalyst selectively afforded pyrrolidines in high yields at 45 °C.

Catalytic intermolecular hydroaminations of unactivated olefins with secondary alkyl amines

The intermolecular hydroamination of unactivated alkenes with simple dialkyl amines remains an unsolved problem in organic synthesis. We report a catalytic protocol for efficient additions of cyclic and acyclic secondary alkyl amines to a wide range of alkyl olefins with complete anti-Markovnikov regioselectivity. In this process, carbon-nitrogen bond formation proceeds through a key aminium radical cation intermediate that is generated via electron transfer between an excited-state iridium photocatalyst and an amine substrate. These reactions are redox-neutral and completely atom-economical, exhibit broad functional group tolerance, and occur readily at room temperature under visible light irradiation. Certain tertiary amine products generated through this method are formally endergonic relative to their constituent olefin and amine starting materials and thus are not accessible via direct coupling with conventional ground-state catalysts.

Br?nsted acid-catalysed intramolecular hydroamination of unactivated alkenes: metal triflates as an in situ source of triflic acid

Hydroamination of alkenes or alkynes is one of the most straightforward methods to form C-N bonds and nitrogen-containing heterocycles. A simple Lewis acid Al(OTf)3 was found to be an effective precatalyst for the hydroamination of unactivated

Ruthenium-Catalyzed Amination of Secondary Alcohols Using Borrowing Hydrogen Methodology

A new ruthenium complex catalyzes the amination of primary and secondary alcohols and the regioselective mono- and sequential diamination of diols via the borrowing hydrogen pathway. Several variations on new intra- and intermolecular cyclizations of aminoalcohols, diols, and diamines lead to heterocyclic ring systems.

Unusual NHC-Iridium(I) Complexes and Their Use in the Intramolecular Hydroamination of Unactivated Aminoalkenes

N-heterocyclic carbene (NHC) ligands with naphthyl side chains were employed for the synthesis of unsaturated, yet isolable [(NHC)Ir(cod)]+ (cod=1,5-cyclooctadiene) complexes. These compounds are stabilised by an interaction of the aromatic win

Dissociation or cyclization: Options for a triad of radicals released from oxime carbamates

A set of oxime carbamates having N-alkyl and N,N-dialkyl substituents were prepared via carbonyldiimidazole intermediates. It was shown by EPR spectroscopy that they underwent clean homolysis of their N-O bonds upon UV photolysis. During photolysis of acetophenone O-allylcarbamoyl oxime, the corresponding oxazolidin-2-onylmethyl radical was detected by EPR spectroscopy, providing the first evidence that N-monosubstituted carbamoyloxyl radicals can hold their structural integrity. N,N-Disubstituted carbamoyloxyl radicals dissociated rapidly at the lowest accessible temperatures. Above room temperature, both types of oxime carbamate acted as selective new precursors for aminyl and iminyl radicals. Rate parameters were measured for 5-exo cyclization of N-benzyl-N-pent-4-enylaminyl radicals; the rate constant was smaller than for C-centered and O-centered analogues. Oxime carbamates derived from the volatile diethylamine afforded aryliminyl radicals that proved convenient for phenanthridine preparations.