82959-87-3

Usage

Uses

Used in Organic Synthesis:
3-Pyrrolidinecarboxylic acid, 2-phenyl-, methyl ester, cisis used as a building block in organic synthesis for the creation of various complex organic molecules. Its unique structure allows for the formation of new chemical entities through reactions such as esterification, amidation, and other condensation processes.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 3-Pyrrolidinecarboxylic acid, 2-phenyl-, methyl ester, cisis utilized as a pharmaceutical intermediate. It plays a crucial role in the synthesis of drug candidates, contributing to the development of new medications with potential therapeutic benefits.
Used in Research Applications:
3-Pyrrolidinecarboxylic acid, 2-phenyl-, methyl ester, cisis also employed in research settings for the exploration of its chemical properties and potential applications. Researchers use 3-Pyrrolidinecarboxylic acid, 2-phenyl-, methyl ester, cis- to study its reactivity, stability, and interactions with other molecules, which can lead to the discovery of novel applications in various fields.
It is essential to handle 3-Pyrrolidinecarboxylic acid, 2-phenyl-, methyl ester, ciswith care and follow appropriate safety protocols due to its potential hazards. Proper handling and storage are crucial to ensure the safety of individuals working with this chemical compound.

Upstream product

• 57402-97-8 N-<(trimethylsilyl)methyl>benzaldimine 
• 292638-85-8 acrylic acid methyl ester 
• 109-69-3 n-Butyl chloride 
• 90606-10-3 (E)-N-(phenylmethylene)-1-(trimethylsilyl)methylamine 
• 55-21-0 benzamide 
• 98-88-4 benzoyl chloride 
• 71572-22-0 N-[(trimethylsilyl)methyl]benzamide 
• 138495-07-5 4-{[1-Phenyl-meth-(E)-ylidene]-amino}-butyric acid methyl ester 
• 13031-60-2 methyl γ-aminobutyrate hydrochloride 
• 883627-59-6 [1-Phenyl-meth-(Z)-ylidene]-trimethylsilanylmethyl-amine 
• 100-52-7 benzaldehyde 
• 34039-84-4 α-(benzylideneamino)acetonitrile 
• 3251-07-8 methyl 4-aminobutyrate 
• 138495-07-5 (E)-methyl 4-(benzylideneamino)butanoate 

Downstream Products

• 79962-72-4 (2S,3S)-1-Benzoyl-2-phenyl-pyrrolidine-3-carboxylic acid methyl ester 
• 79962-72-4 (2S,3R)-1-Benzoyl-2-phenyl-pyrrolidine-3-carboxylic acid methyl ester 

Relevant academic research and scientific papers

One-Pot Reductive 1,3-Dipolar Cycloaddition of Secondary Amides: A Two-Step Transformation of Primary Amides

The one-pot reductive 1,3-dipolar cycloaddition of secondary aromatic N-(trimethylsilylmethyl)amides with reactive dipolarophiles is reported. The method relies on the in situ generation of nonstabilized NH azomethine ylide dipoles via amide activation with triflic anhydride, partial reduction with 1,1,3,3-tetramethyldisiloxane (TMDS), and desilylation with cesium fluoride (CsF). Running under mild conditions, the reaction tolerated several sensitive functional groups and provided cycloadducts in 71-93% yields. The use of less reactive dipolarophile methyl acrylate led to the cycloadduct in only 40% yield. A (Z) geometric intermediate of NH-azomethine 1,3-dipole was postulated to account for the observed higher yields and higher cis diastereoselectivity for the substrates bearing an electron-withdrawing group. This model features an unconventional cyclic transition state via carbanion-aryl ring interaction. Because the starting secondary amides can be prepared from common primary amides, the current method also constitutes a two-step transformation of primary amides.

Rhodium-Catalyzed Intramolecular C-H Bond Activation with Triazoles: Preparation of Stereodefined Pyrrolidines and Other Related Cyclic Compounds

On treatment of triazoles having an N-sulfonyl-protected benzylamine moiety with [Rh2(C7H15CO2)4], intramolecular C-H bond insertion takes place at the benzylic position to give cis-N-sulfonyl-2-aryl-3-[(sulfonylimino)methyl]pyrrolidines in good yields and with highly stereoselectivities. Analogously, the similar treatment of triazoles having an ether or even an alkyl moiety affords 2-alkyl- or 2-aryl-3-[(sulfonylimino)methyl]tetrahydrofurans or a 2-alkyl-3-[(sulfonylimino)methyl]cyclopentane in good yields. Three is a magic number: On treatment of triazoles with [Rh2(C7H15CO2)4], the rhodium catalyst plays three roles, denitrogenation, C-H bond activation, and stereoselective cyclization, providing a new method for heterocycle synthesis. Intramolecular C-H bond insertion takes place at the benzylic position to give pyrrolidines and related heterocycles in good yields.

Synthesis of β-prolinols via [3+2] cycloaddition and one-pot programmed reduction: Valuable building blocks for polyheterocycles

A novel two-step synthesis of multisubstituted β-prolinols has been developed, featuring a [3+2] cycloaddition of azomethine ylides and a programmed reduction triggered by the combination of borane and lithium aluminum hydride (LAH). β-Prolinols are shown to be valuable building blocks for polyheterocycles.

The Cyano Group as a Traceless Activation Group for the Intermolecular [3+2] Cycloaddition of Azomethine Ylides: A Five-Step Synthesis of (±)-Isoretronecanol

The cyano group was used as a traceless activation group for the [3+2] cycloaddition of azomethine ylides in a two-step process, thereby providing a highly effective approach to 5-unsubstituted pyrrolidines. The transformation includes the silver acetate

Synthesis of cis-2-aryl-3-pyrrolidine carboxylic esters via diastereoselective cyclization of γ-imino esters using a TiCl 4/Et3N reagent system

Facile synthesis of cis-2-aryl-3-pyrrolidine carboxylates from readily accessible γ-imino esters by intramolecular cyclization mediated by a TiCl4/Et3N reagent system is described.

One-Pot Synthesis of N-Alkylpyrrolidines by 1,3-Dipolar Cycloaddition

N-Alkylpyrrolidines were obtained by one-pot synthesis through 1,3-dipolar cycloaddition of the N-alkylazomethine ylide intermediates generated from N-(benzylidene)trimethylsilylmethylamine and alkyl halide or tosylate.

The Origin of Regio- and Stereoselectivities in 1,3-Cycloadditions of Azomethine Ylides Generated from N-(Benzylidene)trimethylsilylmethylamine and the Related Compounds

The frontier molecular orbital theory (ab initio procedures) was found to clearly explain the regio- and stereoselectivities in 1,3-dipolar cycloadditions of the azomethine ylides to conjugated olefins yielding the pyrrolidines.

Trimethylsilyl Triflate-Catalyzed 1,3-Dipolar Cycloaddition Leading to N-Unsubstituted Pyrrolidines

Dipolar cycloaddition of an intermediary N-trimethylsilyltrimethylsilylmethyliminium salt formed from N-(benzylidene)trimethylsilylmethylamine by the catalytical action of trimethylsilyl triflate to conjugated alkene or alkyne gave N-unsubstituted pyrroli

1,3-DIPOLAR CYCLOADDITION LEADING TO N-ALKYLPYRROLIDINES

1,3-Dipolar cycloaddition of an intermediary methyleneiminium ylide formed from N-(benzylidene)trimethylsilylmethylamine and alkyl halide to conjugated olefinic dipolarophiles has been found to give N-alkylpyrrolidines.KEYWORDS - N-alkylpyrrolidine; N-unsubstituted pyrrolidine; 1,3-dipolar cycloaddition; N-alkyltrimethylsilylmethyliminium salt; methyleneiminium ylide

A NEW TRIMETHYLSILYL TRIFLATE-CATALYZED 1,3-DIPOLAR CYCLOADDITION LEADING TO PYRROLIDINES

Pyrrolidines were obtained by a new, trimethylsilyl triflate-catalyzed cycloaddition of an intermediary N-trimethylsilylated methylene-iminium ylide, a 1,3 dipole, to olefinic and acetylenic dipolarophiles.