135339-67-2

Basic information

• Product Name: 1-Pyrrolidinecarboxylic acid, 2-[[[(1S)-1-phenylethyl]amino]carbonyl]-, 1,1-dimethylethyl ester, (2S)-
• CAS NO: 135339-67-2
• Molecular Formula: C18H26N2O3
• Molecular Weight: 318.416
• Mol File: 135339-67-2.mol
• Article Data: 12

Chemical Properties

• CAS DataBase Reference: 1-Pyrrolidinecarboxylic acid, 2-[[[(1S)-1-phenylethyl]amino]carbonyl]-, 1,1-dimethylethyl ester, (2S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Pyrrolidinecarboxylic acid, 2-[[[(1S)-1-phenylethyl]amino]carbonyl]-, 1,1-dimethylethyl ester, (2S)-(135339-67-2)
• EPA Substance Registry System: 1-Pyrrolidinecarboxylic acid, 2-[[[(1S)-1-phenylethyl]amino]carbonyl]-, 1,1-dimethylethyl ester, (2S)-(135339-67-2)

Safety Data

• Hazardous Substances Data: 135339-67-2(Hazardous Substances Data)

Usage

Molecular structure

Consists of a pyrrolidine ring, a phenylethyl group, and a carboxylic acid.

Ester form

Present as a 1,1-dimethylethyl ester.

Chirality

Compound is chiral, meaning it has a specific three-dimensional arrangement of atoms.

Stereochemistry

Designated as (2S)-, indicating the orientation of the chiral center.

Industry applications

Likely used in pharmaceutical or chemical industries due to its specific properties.

Potential hazards

Exact functions, uses, and hazards require further investigation and analysis.

Upstream product

• 147-85-3 L-proline 
• 24424-99-5 di-tert-butyl dicarbonate 
• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 2627-86-3 (S)-1-phenyl-ethylamine 
• 141874-26-2 N-Boc-(S)-proline chloride 
• 133010-05-6 tert-butyl 2-(fluorocarbonyl)pyrrolidine-1-carboxylate 
• 7531-52-4 L-prolinamide 

Downstream Products

• 1229277-96-6 (2S)-2-[methyl-((1S)-1-phenylethyl)-carbamoyl]-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 904326-10-9 (2S)-N-[(1S)-1-phenylethyl]pyrrolidine-2-carbothioamide 
• 149673-13-2 (2S)-pyrrolidine-2-carboxylic acid N-((1S)-1-phenyl-ethyl)-amide 
• 914097-68-0 tert-butyl (2S)-2-{[(1S)-1-phenylethyl]thiocarbamoyl}pyrrolidine-1-carboxylate 

Relevant articles and documents

L-prolinethioamides - Efficient organocatalysts for the direct asymmetric aldol reaction

A series of novel L-proline derived thioamides has been synthesised. They have been evaluated as organocatalysts in the direct asymmetric aldol reaction for the first time. Thioamides exhibit catalytic ability higher than proline itself and the model aldol reaction of 4-cyanobenzaldehyde with acetone proceeds well in the presence of 5 mol % of catalyst (ee up to 100%). Other aromatic aldehydes gave aldol products with high ees and moderate yields. Small changes in the catalyst's structure [e.g., N-Bn versus N-CH(CH3)Ph] as well as the addition of an acid have a profound effect on their activity. The unexpected formation of the catalyst-derived cyclic adducts was observed and their reactivity was established giving valuable insight into the course of the reaction.

Highly modular dipeptide-like organocatalysts for direct asymmetric aldol reactions in brine

A novel series of dipeptide-like organocatalysts derived from proline, amino acids and primary amines have been prepared for direct asymmetric aldol reactions between various aromatic aldehydes and acetone to afford aldol products in good yields (up to 82%) and moderate enantioselectivities (up to 67% ee) with only 1 mol% of catalyst-loading in brine. Under the same conditions, the direct asymmetric aldol reactions of aromatic aldehydes and cyclohexanone give aldol products with high yields (up to 91%) and moderate to good enantioselectivities (up to 88% ee) and excellent diastereoselectivities (up to 99% dr). These organocatalysts are easily synthesized from commercially available materials in multi-gram scale with high modularity in their structural and stereogenic properties.

Direct amide formation using radiofrequency heating

We present a simple method for direct and solvent-free formation of amides from carboxylic acids and amines using radiofrequency heating. The direct energy coupling of the AC magnetic field via nickel ferrite magnetic nanoparticles enables fast and controllable heating, as well as enabling facile work-up via magnetic separation.