82959-87-3

Basic information

• Product Name: 3-Pyrrolidinecarboxylic acid, 2-phenyl-, Methyl ester, cis-
• Synonyms: 3-Pyrrolidinecarboxylic acid, 2-phenyl-, Methyl ester, cis-;cis-2-Phenyl-pyrrolidine-3-carboxylic acid methyl ester
• CAS NO: 82959-87-3
• Molecular Formula: C₁₂H₁₅NO₂
• Molecular Weight: 205.253
• Mol File: 82959-87-3.mol
• Article Data: 10

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-Pyrrolidinecarboxylic acid, 2-phenyl-, Methyl ester, cis-(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Pyrrolidinecarboxylic acid, 2-phenyl-, Methyl ester, cis-(82959-87-3)
• EPA Substance Registry System: 3-Pyrrolidinecarboxylic acid, 2-phenyl-, Methyl ester, cis-(82959-87-3)

Safety Data

• Hazardous Substances Data: 82959-87-3(Hazardous Substances Data)

Usage

General Description

3-Pyrrolidinecarboxylic acid, 2-phenyl-, methyl ester, cis- is a chemical compound with the molecular formula C13H17NO2. It is a methyl ester of 3-pyrrolidinecarboxylic acid, 2-phenyl- in cis configuration. 3-Pyrrolidinecarboxylic acid, 2-phenyl-, methyl ester, cis- is used in various industrial and research applications, including as a building block in organic synthesis and as a pharmaceutical intermediate. It has potential uses in the production of drugs and other biologically active compounds. However, it is important to handle this chemical with caution and adhere to proper safety protocols due to its potential hazards.

Upstream product

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

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 articles and documents

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.

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.

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.