118758-47-7

Basic information

• Product Name: (2R,3R)-3-Methylpyrrolidine-2-carboxylic acid
• Synonyms: (2R,3R)-3-Methylpyrrolidine-2-carboxylic acid
• CAS NO: 118758-47-7
• Molecular Formula: C6H11NO2
• Molecular Weight: 129.16
• Mol File: 118758-47-7.mol
• Article Data: 5

Chemical Properties

• Melting Point: 243-248℃
• Appearance: /
• Density: 1.104
• CAS DataBase Reference: (2R,3R)-3-Methylpyrrolidine-2-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3R)-3-Methylpyrrolidine-2-carboxylic acid(118758-47-7)
• EPA Substance Registry System: (2R,3R)-3-Methylpyrrolidine-2-carboxylic acid(118758-47-7)

Safety Data

• Hazardous Substances Data: 118758-47-7(Hazardous Substances Data)

Usage

Description

(2R,3R)-3-Methylpyrrolidine-2-carboxylic acid is a chemical compound with the molecular formula C7H13NO2. It is a derivative of pyrrolidine, a five-membered heterocyclic ring containing one nitrogen atom. (2R,3R)-3-Methylpyrrolidine-2-carboxylic acid exists as a colorless liquid and is characterized by its specific (2R,3R) stereochemistry, which refers to the orientation of the substituent groups around the asymmetric carbon atoms. This feature is crucial for its applications and reactivity in chemical processes.

Uses

Used in Pharmaceutical Industry:
(2R,3R)-3-Methylpyrrolidine-2-carboxylic acid serves as an important building block in the synthesis of various pharmaceuticals. Its unique stereochemistry and structural properties make it a valuable component in the development of new drugs, contributing to the creation of molecules with specific therapeutic effects and improved pharmacological properties.
Used in Agrochemical Industry:
In the agrochemical sector, (2R,3R)-3-Methylpyrrolidine-2-carboxylic acid is utilized in the synthesis of compounds that have applications in agriculture, such as pesticides and herbicides. Its role in these syntheses can lead to the development of more effective and targeted agrochemicals that can enhance crop protection and yield.
Used in Organic Synthesis:
(2R,3R)-3-Methylpyrrolidine-2-carboxylic acid is also used as a versatile building block for the production of a wide range of organic compounds. Its ability to participate in various chemical reactions makes it a useful intermediate in the synthesis of specialty chemicals, fragrances, and other fine chemicals that have applications across different industries.

Upstream product

• 131683-39-1 (2S,3S)-1-(2,2-Dimethyl-propionyl)-3-methyl-pyrrolidine-2-carbothioic acid S-(3-mercapto-propyl) ester 
• 623-43-8 crotonic acid methyl ester 
• 110269-68-6 tert-butyl ((1R,4R)-bornylideneamino)acetate 
• 127811-84-1 2-(4-azidobut-1-ylidene)-1,3-dithiane 
• 75041-78-0 N-pivaloyl proline 
• 123-73-9 trans-Crotonaldehyde 
• 1417600-55-5 (2R,3R)-1-[(benzyloxy)carbonyl]-3-methylpyrrolidine-2-carboxylic acid 
• 131669-62-0 2-(N-Pivaloyl-3-methylpyrrolidin-2-ylidene)-1,3-dithiane 
• 131669-61-9 2-<1-(2,2-dimethylpropanoyl)pyrrolidin-2-ylidene>-1,3-dithiane 
• 98353-14-1 Methyl N-pivaloylprolinate 

Relevant articles and documents

Organocatalytic michael addition of nitro esters to a,β-unsaturated aldehydes: Towards the enantioselective synthesis of trans-3-substituted proline derivatives

A facile five-step strategy has been developed for the enantioselective synthesis of trans-3- substituted proline derivatives with high diasteroselectivity (dr>20:1) and enantioselectivity (up to 97% ee). The key step is the asymmetric organocatalytic Michael addition of nitro esters to a,β-unsaturated aldehydes, which affords the chiral Michael adducts in high yields (up to 96%) and excellent enantioselectivity (up to 99% ee) by using diaryl- ACHTUNGTRENUNGprolinol silyl ether as the organocatalyst.

Highly Diasteroselective Michael-Addition of Lithiated Camphor Imines of Glycine Esters to α,β-Unsaturated Esters. Synthesis of Optically Pure 5-Oxo-2,4-pyrrolidinedicarboxylates of Unnatural Stereochemistry

The lithium enolates of camphor imines of glycine esters underwent highly diastereoselective Michael additions to the α,β-unsaturated esters.The tightly chelated structure of the Z,E enolates and the selective approach of the α,β-unsaturated esters to the

Synthesis of Enantio- and Diastereoiso-merically Pure Substituted Prolines via Condensation of Glycine with Olefins Activated by a Carbonyl Group

The glycine fragment in the nickel(II) complex (1) formed from the Schiff's base of glycine and (S)-o-benzophenone (2) undergoes base-catalysed Michael addition to acrylaldehyde, α-methylacrylaldehyde, (E)-crotonaldehyde, (E)-cinnamaldehyde, and methyl vinyl ketone.No products of 1,2-addition were found in the Et3N-catalysed reactions.Addition followed by epimerization of the isomeric complexes proceeds with high diastereoselectivity at Cα (90percent) and Cβ of the corresponding amino acid side chains.After chromatographic separation, the diastereoisomerically pure complexes were decomposed and the resulting dihydropyrrole-2-carboxylic acids reduced with NaBH3CN to give (S)-proline, trans-3-methyl-(S)-proline, trans-5-phenyl-(S)-proline, and a mixture of cis- and trans-5-methyl-(S)-prolines.The chiral auxiliary (2) was recovered in 80-90percent yield.