35840-91-6

Usage

Uses

Used in Pharmaceutical Industry:
2-BENZYLPYRROLIDINE is used as an intermediate in the synthesis of various pharmaceuticals for its ability to facilitate the creation of complex organic molecules with specific chiral properties. This is crucial in the development of drugs that require precise stereochemistry for optimal efficacy and safety.
Used in Agrochemical Industry:
In the agrochemical sector, 2-BENZYLPYRROLIDINE is utilized as a building block for the production of active ingredients in pesticides and other crop protection agents. Its versatility allows for the design of molecules with targeted biological activity against pests and diseases.
Used in Fragrance Industry:
2-BENZYLPYRROLIDINE is employed as a component in the creation of fragrances, where its aromatic properties contribute to the development of unique scents and perfumes. Its use in this industry underscores the compound's ability to influence the olfactory characteristics of final products.
Used in Specialty Chemicals Production:
2-BENZYLPYRROLIDINE is used as a key intermediate in the synthesis of specialty chemicals, which are often required for niche applications in various industries. Its role in this context highlights the compound's adaptability and the breadth of its potential uses in chemical manufacturing.
Used in Asymmetric Synthesis:
2-BENZYLPYRROLIDINE is used as a chiral auxiliary in asymmetric synthesis, a technique that is vital for producing enantiomerically pure compounds. This application is particularly important in the pharmaceutical industry, where the desired biological activity of a drug is often associated with a specific enantiomer.

InChI:InChI=1/C11H15N/c1-2-5-10(6-3-1)9-11-7-4-8-12-11/h1-3,5-6,11-12H,4,7-9H2

Upstream product

• 69311-30-4 5-benzyl-3,4-dihydro-2H-pyrrole 
• 89656-30-4 [1-(2-Benzyl-pyrrolidin-1-yl)-meth-(E)-ylidene]-tert-butyl-amine 
• 138084-62-5 2,2,5,5-tetrametyl-1-aza-2,5-disilacyclopentane-1-propyl magnesium bromide 
• 95092-10-7 N-methoxy-N-methyl-2-phenylacetamide 
• 89656-30-4 [1-(2-Benzyl-pyrrolidin-1-yl)-meth-(E)-ylidene]-tert-butyl-amine 
• 144688-81-3 α-benzyl-N-tert-butoxycarbonylpyrrolidine 
• 882696-35-7 2-benzyl-1-(phenylsilyl)pyrrolidine 
• 100-52-7 benzaldehyde 
• 119793-72-5 (E)-2-(3-phenyl-allyl) malonic acid dimethyl ester 
• 33599-84-7 methyl (E)-5-phenyl-4-pentenoate 
• 21087-29-6 trans-3-phenylprop-2-enyl chloride 
• 5724-81-2 1-pyrroline 
• 6921-34-2 benzylmagnesium chloride 
• 1119-51-3 bromopentene 

Downstream Products

• 804518-87-4 2-[(R)-3-(2-Benzyl-pyrrolidin-1-yl)-2-hydroxy-propoxy]-6-chloro-benzonitrile 
• 66163-11-9 2-benzyl-1-cyclopropylcarbonylpyrrolidine 
• 288082-58-6 C₃₀H₃₄N₆O₃ 
• 66163-08-4 1-(2-(4-nitrobenzyl)pyrrolidin-1-yl)ethanone 
• 66163-10-8 1-ethyl-2-(4-aminobenzyl)pyrrolidine 
• 66163-12-0 2-benzyl-1-cyclopropylmethylpyrrolidine 
• 14293-06-2 5-(phenylmethyl)pyrrolidin-2-one 
• 144688-81-3 α-benzyl-N-tert-butoxycarbonylpyrrolidine 

Relevant academic research and scientific papers

Construction of azacycles by intramolecular amination of organoboronates and organobis(boronates)

Intramolecular amination of organoboronates occurs with a 1,2-metalate shift of an aminoboron ate complex to form azetidines, pyrrolidines, and piperidines. Bis(boronates) undergo site-selective amination to form boronate-containing azacycles. Enantiomerically enriched azacycles are formed with high stereospecificity.

O-benzoylhydroxylamines as alkyl nitrene precursors: Synthesis of saturated N-heterocycles from primary amines

We introduce O-benzoylhydroxylamines as competent alkyl nitrene precursors. The combination of readily available, stable substrates and a proficient rhodium catalyst provides a straightforward means for the construction of various pyrrolidine rings from the corresponding primary amines. Preliminary mechanistic investigation suggests that the structure of the nitrene precursor plays a role in determining the nature of the resulting reactive intermediate.

Basicities and Nucleophilicities of Pyrrolidines and Imidazolidinones Used as Organocatalysts

The Br?nsted basicities pKaH (i.e., pKa of the conjugate acids) of 32 pyrrolidines and imidazolidinones, commonly used in organocatalytic reactions, have been determined photometrically in acetonitrile solution using CH acids as indicators. Most investigated pyrrolidines have basicities in the range 16 aH aH aH 12.6) and the 2-imidazoliummethyl-substituted pyrrolidine A21 (pKaH 11.1) are outside the typical range for pyrrolidines with basicities comparable to those of imidazolidinones. Kinetics of the reactions of these 32 organocatalysts with benzhydrylium ions (Ar2CH+) and structurally related quinone methides, common reference electrophiles for quantifying nucleophilic reactivities, have been measured photometrically. Most reactions followed second-order kinetics, first order in amine and first order in electrophile. More complex kinetics were observed for the reactions of imidazolidinones and several pyrrolidines carrying bulky 2-substituents, due to reversibility of the initial attack of the amines at the electrophiles followed by rate-determining deprotonation of the intermediate ammonium ions. In the presence of 2,4,6-collidine or 2,6-di-tert-butyl-4-methyl-pyridine, the deprotonation of the initial adducts became faster, which allowed the rate of the attack of the amines at the electrophiles to be determined. The resulting second-order rate constants k2 followed the correlation log?k2(20 °C) = sN(N + E), where electrophiles are characterized by one parameter (E) and nucleophiles are characterized by the two solvent-dependent parameters N and sN. In this way, the organocatalysts A1-A32 were integrated in our comprehensive nucleophilicity scale, which compares n-, -, and σ-nucleophiles. The nucleophilic reactivities of the title compounds correlate only poorly with their Br?nsted basicities.

α-Functionalization of Cyclic Secondary Amines: Lewis Acid Promoted Addition of Organometallics to Transient Imines

Cyclic imines, generated in situ from their corresponding N-lithiated amines and a ketone hydride acceptor, undergo reactions with a range of organometallic nucleophiles to generate α-functionalized amines in a single operation. Activation of the transient imines by Lewis acids that are compatible with the presence of lithium alkoxides was found to be crucial to accommodate a broad range of nucleophiles including lithium acetylides, Grignard reagents, and aryllithiums with attenuated reactivities.

Enantioselective synthesis of amines by combining photoredox and enzymatic catalysis in a cyclic reaction network

Visible light-driven reduction of imines to enantioenriched amines in aqueous solution is demonstrated for the first time. Excitation of a new water-soluble variant of the widely used [Ir(ppy)3] (ppy = 2-phenylpyridine) photosensitizer in the p

Tf2O-Promoted Intramolecular Schmidt Reaction of the ω-Azido Carboxylic Acids

A designed Tf2O-promoted intramolecular Schmidt reaction of 2-substituted ω-azido carboxylic acids was demonstrated. Tf2O was used as an activation reagent for the carboxylic acid, and ω-azido anhydride was in situ generated, releasing a molecular TfOH, which acted as an acid promoter for the Schmidt process. A series of 2-substituted pyrrolidines was produced and acetylated for better purification. The strategy was also efficient for conversion of a 4-substituted ω-azido carboxylic acid to the tricyclic lactam.

Redox-Triggered α-C-H Functionalization of Pyrrolidines: Synthesis of Unsymmetrically 2,5-Disubstituted Pyrrolidines

By using o-benzoquinone as an internal oxidant, the regio- and diastereoselective functionalization of the secondary over the tertiary α-C-H bond of 2-substituted pyrrolidines is first realized. Subsequent intermolecular addition of a nucleophile to the g

Catalytic olefin hydroamination with aminium radical cations: A photoredox method for direct C-N bond formation

While olefin amination with aminium radical cations is a classical method for C-N bond formation, catalytic variants that utilize simple 2° amine precursors remain largely undeveloped. Herein we report a new visible-light photoredox protocol for the intramolecular anti-Markovnikov hydroamination of aryl olefins that proceeds through catalytically generated aminium radical intermediates. Mechanistic studies are consistent with a process involving amine oxidation via electron transfer, turnover-limiting C-N bond formation, and a second electron transfer step to reduce a carbon-centered radical, rendering the overall process redox-neutral. A range of structurally diverse N-aryl heterocycles can be prepared in good to excellent yields under conditions significantly milder than those required by conventional aminium-based protocols.

HETEROCYCLIC COMPOUNDS AND METHODS FOR THEIR USE

The present invention relates to heterocyclic compounds useful for antagonising angiotensin II Type 2 (AT2) receptor. More particularly the invention relates to pyrrolidine and azetidine compounds, compositions containing them and their use in methods of treating or preventing disorders or diseases associated with AT2 receptor function including neuropathic pain, inflammatory pain, conditions associated with neuronal hypersensitivity, impaired nerve conduction velocity, cell proliferation disorders, disorders associated with an imbalance between bone resorption and bone formation and disorders associated with aberrant nerve regeneration.

Synthesis of 2-substituted pyrrolidines from nitriles

A novel and synthetically facile production of 2-substituted pyrrolidines from commercially available nitriles is reported herein. This methodology is operationally simple, and only requires the use of an extraction and a single chromatographic purificati