955-40-8

Usage

Uses

Used in Organic Synthesis:
N-Benzyl-L-proline ethyl ester is used as a chiral building block for the synthesis of various organic compounds. Its unique structure and properties make it a valuable component in the development of new pharmaceuticals and other chemical products.
Used in Pharmaceutical Industry:
N-Benzyl-L-proline ethyl ester is used as a precursor in the preparation of proline-containing peptides and drugs. Its presence in these compounds can contribute to their biological activity and therapeutic potential.
Used in Enzyme Inhibition:
N-Benzyl-L-proline ethyl ester has been studied for its potential to inhibit certain enzymes, which could have implications for the treatment of various diseases and conditions.
Used in Anti-inflammatory Applications:
N-Benzyl-L-proline ethyl ester has been investigated for its anti-inflammatory properties, which could make it a useful agent in the treatment of inflammation-related disorders.
Used in Neuroprotective Applications:
N-Benzyl-L-proline ethyl ester has also been studied for its potential neuroprotective effects, suggesting that it may have a role in the prevention or treatment of neurodegenerative diseases.
Note: The specific application reasons and industries for N-Benzyl-L-proline ethyl ester may vary depending on the context and ongoing research. The uses listed above are based on the provided materials and are subject to further investigation and development.

InChI:InChI=1/C14H19NO2/c1-2-17-14(16)13-9-6-10-15(13)11-12-7-4-3-5-8-12/h3-5,7-8,13H,2,6,9-11H2,1H3/t13-/m0/s1

Upstream product

• 6738-17-6 O-benzyl-N,N'-dicyclohexylisourea 
• 5817-26-5 ethyl (2S)-pyrrolidine-2-carboxylate 
• 67-56-1 methanol 
• 100-39-0 benzyl bromide 
• 64-17-5 ethanol 
• 31795-93-4 N-benzyl-L-proline 
• 147-85-3 L-proline 

Downstream Products

• 118970-94-8 (S)-(-)-1-benzyl-2-(1-hydroxy-1-butylpentyl)-pyrrolidine 
• 118970-95-9 (S)-1-benzyl-2-(hydroxydiphenylmethyl)pyrrolidine 
• 123476-57-3 ethyl 1-benzyl-1H-pyrrole-2-carboxylate 
• 131180-63-7 bis(3,5-dimethylphenyl)-(S)-pyrrolidin-2-ylmethanol 
• 131180-65-9 (S)-α,α-Bis(4-(trifluoromethyl)phenyl)-2-pyrrolidinemethanol 
• 866929-76-2 1-((S)-1-benzyl-pyrrolidin-2-yl)-cyclopropanol 
• 110529-27-6 (S)-1-[(2S)-1-benzylpyrrolidin-2-yl](phenyl)methanol 
• 220058-21-9 (R)-1-[(2S)-1-benzylpyrrolidin-2-yl](phenyl)methanol 
• 911429-36-2 (2S)-1-benzylpyrrolidine-2-carbohydrazide 
• 114883-84-0 C₁₂H₁₆N₂O 
• 114883-85-1 (S)-1-benzyl-pyrrolidine-2-carboxylic acid amide 
• 5817-26-5 ethyl (2S)-pyrrolidine-2-carboxylate 
• 1383720-75-9 (2S)-1-benzyl-N'-[(E)-(4-methoxyphenyl)methylidene]pyrrolidine-2-carbohydrazide 
• 1383720-78-2 (2S)-1-benzyl-N'-[(E)-2-furylmethylidene]pyrrolidine-2-carbohydrazide 

Relevant academic research and scientific papers

Catalytic asymmetric aldol-type reaction of zinc enolate equivalent of amides

Treatment of phenyl isocyanate with bis(iodozincio)methane gave a zinciomethylenated product, which acts as an amide-enoate equivalent. It did not react with an aldehyde efficiently, but gave the corresponding adduct in good yield in the presence of an aminoalcohol. Use of a catalytic amount of chiral aminoalcohol led the process to the catalytic asymmetric Aldol-type reaction.

Reactions of amines and hydrazides derived from L-proline with dialkyl dicyanofumarates

The reaction of prolinamine derivatives (8a,b) and dialkyl dicyanofumarates (1) in dichloromethane at room temperature leads to the optically active enamines (10). Whereas products (10) in the case of 1-benzyl prolinamine (8a) are stable compounds, the corresponding enamines obtained from the non-protected prolinamine (8b) smoothly undergo a cyclocondensation at room temperature to give perhydropyrrolo[1,2-a]pyrazine derivatives (11). The molecular structure of 11a was established by X-Ray crystallography. In analogy to 8a, 1-benzyl prolinehydrazide (9a) and 1b in dichloromethane react to yield the enehydrazine (12b). On the other hand, the reaction of 9a and 1 in methanol at room temperature leads to the corresponding dialkyl 3-amino-1H-pyrazole- 4,5-dicarboxylates (13) and methyl 1-benzylprolinate (14b) Via a stepwise mechanism. The analogous reaction was observed between a 3-oxidoimidazole-4- carbohydrazide (15) and 1b.

Studies on the synthesis and some reactions of (S)-proline hydrazides

A convenient synthesis of (S)-proline hydrazide 2a via the reaction of ethyl (S)-N-benzylprolinate with hydrazine hydrate and subsequent deprotection of (S)-N-benzyl proline hydrazide 5 is described. The latter, in methanolic solution, reacted with aromatic aldehydes as well as with cycloaliphatic ketones at room temperature to give the corresponding hydrazones of type 7 in good yields. The structure of the product with furan-2-carbaldehyde 7b, proving the (E)-configuration of the hydrazone, was established by X-ray crystallography. In the case of the unprotected (S)-proline hydrazide 2a, the analogous reaction with aromatic aldehydes led either to the expected hydrazones 7 or the 1H-pyrrolo[1,2-c]imidazol-1-one derivatives 8, depending on the reaction conditions. The latter were formed via a secondary cyclocondensation of the initially formed 7 with a second molecule of the aldehyde. Whereas the reaction of (S)-N-benzyl proline hydrazide 5 with butyl isocyanate and isothiocyanate gave the corresponding semicarbazide and thiosemicarbazide, respectively, of type 9, the unprotected (S)-proline hydrazide 2a yielded the 1:2 adducts 10. Thiosemicarbazide 9b underwent cyclization reactions under basic (NaOH) and acidic (H2SO4) conditions to yield (S)-prolinyl- substituted 1,2,4-triazole-3-thione 11 and 1,3,4-thiadiazole-2-amine 12, respectively.

LARGE SCALE PREPARATION OF VERSATILE CHIRAL AUXILIARIES DERIVED FROM (S)-PROLINE

The synthesis of a variety of enantiomerically pure chiral auxiliaries based on (S)-proline and bearing sterically demanding side chains at the pyrrolidine moiety, such as the secondary amines (S)-3,5 and 7 and the hydrazines (S)-6, is described on a molar scale.As key step, the Grignard or RLi addition to the N-benzylated proline ester (S)-1 is used.