130830-78-3

Basic information

• Product Name: 2,4-Pyrrolidinedicarboxylicacid,(2R-cis)-(9CI)
• Synonyms: 2,4-Pyrrolidinedicarboxylicacid,(2R-cis)-(9CI);(2R,4R)-pyrrolidine-2,4-dicarboxylic acid
• CAS NO: 130830-78-3
• Molecular Formula: C6H9NO4
• Molecular Weight: 159.14
• Product Categories: PYRROLE
• Mol File: 130830-78-3.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2,4-Pyrrolidinedicarboxylicacid,(2R-cis)-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-Pyrrolidinedicarboxylicacid,(2R-cis)-(9CI)(130830-78-3)
• EPA Substance Registry System: 2,4-Pyrrolidinedicarboxylicacid,(2R-cis)-(9CI)(130830-78-3)

Safety Data

• Hazardous Substances Data: 130830-78-3(Hazardous Substances Data)

Usage

Class

Organic compounds, specifically alpha amino acids and derivatives

Enantiomer

Naturally occurring amino acid proline

Usage

Chiral building block in the synthesis of pharmaceuticals and biologically active compounds

Therapeutic applications

Potential treatment for various disorders, including Alzheimer's disease and schizophrenia

Other applications

Development of novel materials for drug delivery and tissue engineering applications

Upstream product

• 135999-86-9 2-Acetylamino-2,4-bis-ethoxycarbonyl-4-(toluene-4-sulfonyloxymethyl)-pentanedioic acid diethyl ester 
• 130830-62-5 N-(benzyloxycarbonyl)-trans-4-(tosyloxy)-D-proline ethyl ester 
• 130830-72-7 N-(benzyloxycarbonyl)-cis-4-carboxy-D-proline dimethyl ester 
• 130830-68-1 N-(benzyloxycarbonyl)-cis-4-cyano-D-proline ethyl ester 
• 130930-28-8 N-(benzyloxycarbonyl)-trans-4-hydroxy-D-proline ethyl ester 
• 130830-64-7 N-(benzyloxycarbonyl)-trans-4-acetoxy-D-proline ethyl ester 
• 152170-57-5 (2R,4R)-2-carboxy-4-(2-methylethenyl)-N-vinyloxicarbonylpyrrolidine 
• 188345-79-1 (2R,4R)-1-benzoyl-2,4-pyrrolidinedicarboxylic acid 
• 150562-88-2 (2R,4R)-2-carbomethoxy-4-(2-methylethenyl)-N-vinyloxicarbonylpyrrolidine 
• 130830-76-1 N-(benzyloxycarbonyl)-cis-4-carboxy-D-proline 
• 135999-85-8 tetraethyl 1-acetamido-4-hydroxybutane-1,1,3,3-tetracarboxylate 
• 188345-72-4 2,2,2-trichloroethyl (+/-)-2-azabicyclo[2.2.1]hept-5-ene-2-carboxylate 
• 188345-71-3 2-(tert-butoxycarbonyl)-2-azabicyclo[2.2.1]hept-5-ene 
• 139927-14-3 (+/-)-2-benzoyl-2-azabicyclo<2.2.1>hept-5-ene 

Relevant articles and documents

An enantioselective route to pyrrolidines: Removal of the chiral template from homochiral pyrroloimidazoles

Two-step reductive removal of the chiral template from optically active pyrroloimidazoles, available from 1,3-dipolar cycloaddition of homochiral 4,5-dihydroimidazolium ylides, gives optically active substituted pyrrolidines. Selective manipulation of the substituents affords, e.g., naturally occurring and other optically active proline derivatives, and optically active pyrrolizidines and indolizidines.

Asymmetric Synthesis of α-Amino Acids via Cationic Aza-Cope Rearrengements

Ene-iminium intermediates resulting from reaction between glyoxal and β-amino alcohols rearrange by an aza-Cope process.Three different tandem reactions are thus carried out; their first component is this cationic rearrangement, the second step being either an iminium hydrolysis, a nucleophile-induced ene-iminium cyclization or a Mannich reaction.The last two sequences lead to homochiral proline derivatives.

Synthesis of two cyclic analogs of glutamic acid: cis- and trans-pyrrolidine-2,4-dicarboxylic acids

The tosyl ester 2 of tetraethyl 1-acetamido-4-hydroxybutane- 1,1,3,3-tetracarboxylate gave 4-methylene glutammic acid in 90% yield by refluxing with concentrated HC1. Treatment of 2 with NaOEt, then with refluxing concentrated HC1 gave a 54% yield of cis