135339-67-2

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

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

Downstream Products

• 914097-68-0 tert-butyl (2S)-2-{[(1S)-1-phenylethyl]thiocarbamoyl}pyrrolidine-1-carboxylate 
• 149673-13-2 (2S)-pyrrolidine-2-carboxylic acid N-((1S)-1-phenyl-ethyl)-amide 
• 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 

Relevant academic research and scientific papers

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.

Direct asymmetric aldol reactions catalysed by trans-4-hydroxy-(S)-prolinamide in solvent-free conditions

Direct asymmetric aldol reactions between 4-nitrobenzaldehyde and cyclohexanone were catalysed by trans-4-hydroxy-(S)-prolinamide (10 mol %) in the presence of CH3COOH (10 mol %) as the co-catalyst under solvent-free conditions at 15 °C. (2S,4R)-4-Hydroxy-N-((S)-1-phenylethyl)pyrrolidine-2-carboxamide 2 efficiently catalysed the asymmetric aldol reaction to afford the product in >99% yield and with 95% ee with an anti/syn ratio of 88:12 after 18 h. The additional trans-hydroxyl group on (S)-prolinamide and (S)-1-phenylethylamine both influenced the ee of the predominant anti aldol product. Different benzaldehyde derivatives with cyclohexanone gave the corresponding aldol products in 38-89% yields and with 56-94% ee with anti/syn (100:0-71:29). Catalyst 2 can be used up to 5 continuous cycles for asymmetric aldol reactions between 4-nitrobenzaldehyde and cyclohexanone with overall 91% yield and 86% yield of anti-product with anti/syn (98:2).

A protocol for amide bond formation with electron deficient amines and sterically hindered substrates

A protocol for amide coupling by in situ formation of acyl fluorides and reaction with amines at elevated temperature has been developed and found to be efficient for coupling of sterically hindered substrates and electron deficient amines where standard methods failed.

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.

Structure-reactivity relationships of l-proline derived spirolactams and α-methyl prolinamide organocatalysts in the asymmetric Michael addition reaction of aldehydes to nitroolefins

l-Proline derived spirolactams and α-methyl prolinamides act as organocatalysts for the asymmetric conjugate addition of aldehydes to nitroolefins in excellent yields, with good diastereoselectivity and enantioselectivity. Furthermore, low catalyst loadings (5 mol %) and a low aldehyde molar excess (1.5 M equiv) were achieved.

Enantioselective cyanosilylation of α,α-dialkoxy ketones catalyzed by proline-derived in-situ-prepared N-oxide as bifunctional organocatalyst

Bifunctional N,N′-dioxide catalysts have been developed for highly enantioselective cyanosilylation of α,α-dialkoxy ketones. This process, catalyzed by in-situ-prepared proline-derived N,N′-dioxide 2b, produced the corresponding cyanohydrin trimethylsilyl ethers in excellent yields (up to 99%) with high enantioselectivities (up to 93% ee). A reasonable mechanism was proposed according to the observation of the linear effect, 1H NMR spectra, isolated cyanohydrin, and the roles of the NH and N-oxide moieties of the catalyst.

Chiral bisformamides as effective organocatalysts for the asymmetric one-pot, three-component strecker reaction

(Chemical Equation Presented) C2-symmetric chiral bisformamides have been shown to catalyze the asymmetric one-pot, three-component Strecker reaction, which produced the α-amino nitriles in excellent yields (up to 99%) with good enantioselectiv

Asymmetric direct aldol reaction catalysed by L-prolinethioamides

L-Prolinethioamides have been found to be active catalysts for direct aldol reactions of acetone with aromatic aldehydes, affording aldol products in good yields and with good enantioselectivities. They were prepared from L-proline and simple aliphatic and aromatic amines in optically pure form and in good overall yields. Studies employing ten catalysts allowed us to unequivocally establish the basic principles governing the outcome of the L-prolinethioamide-catalysed aldol reaction. In particular, the catalyst prepared from L-proline and (S)-phenylethylamine catalysed the reaction of acetone with 4-cyanobenzaldehyde in 57 % yield and 93 % ee (100% ee at -78°C). Most importantly, we found that steric interaction between the catalyst and a donor or an acceptor is crucial for the stereoselectivity of the aldol addition, while the unwanted formation of imidazolidinethione (from the catalyst and acetone or an aldehyde) was shown to decrease both the ee and the yield. The influence of the amine moiety (-CSNHR), different solvents and temperatures were studied, and we also found that there is a linear correlation between the optical purity of the catalyst and the ee of the aldol product, which supports the hypothesis that the reaction proceeds by the enamine-imine mechanism, involving only one molecule of the catalyst in the transition state. For the first time, the formation of 1,5-dihydroxypentan-3-one products (double addition products) was studied in detail. By precise optimisation we were able to show that the courses of the reactions of acetone with highly reactive aromatic aldehydes could be manipulated to give either the aldol products or 1,5-dihydroxypentan-3-one derivatives as the major product in moderate ee. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.

Enantioswitchable catalysts for the asymmetric transfer hydrogenation of aryl alkyl ketones

(Chemical Equation Presented) A subtle change in the ligand structure, replacing the carbonyl oxygen with sulfur in simple α-amino acid amides, resulted in a dramatic activity and selectivity improvement in the rhodium- or ruthenium-catalyzed reduction of ketones under hydrogen transfer conditions. In addition, in most cases, a switch of the product's absolute configuration was observed on going from amides to the corresponding thioamides. Under optimized conditions, we obtained the secondary alcohol products in high yield and enantioselectivity (up to 97% ee) using only 0.25 mol % catalyst loading.