955-40-8

Basic information

• Product Name: N-BENZYL-L-PROLINE ETHYL ESTER
• Synonyms: N-BENZYL-L-PROLINE ETHYL ESTER;1-Benzyl-L-proline ethyl ester;N-Benzyl-L-proline ethyl ester 97%
• CAS NO: 955-40-8
• Molecular Formula: C₁₄H₁₉NO₂
• Molecular Weight: 233.31
• Product Categories: Amino Acid Derivatives;Peptide Synthesis;Proline
• Mol File: 955-40-8.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 308.9°C at 760 mmHg
• Flash Point: >230 °F
• Appearance: /
• Density: 1.048 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.15 mm Hg ( 100 °C)
• Refractive Index: n20/D 1.511(lit.)
• Storage Temp.: 2-8°C
• BRN: 5950140
• CAS DataBase Reference: N-BENZYL-L-PROLINE ETHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: N-BENZYL-L-PROLINE ETHYL ESTER(955-40-8)
• EPA Substance Registry System: N-BENZYL-L-PROLINE ETHYL ESTER(955-40-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• RIDADR: 1760
• WGK Germany: 3
• F: 3-10-34
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 955-40-8(Hazardous Substances Data)

Usage

General Description

N-Benzyl-L-proline ethyl ester is a chemical compound that belongs to the class of proline derivatives. It is formed by the esterification of N-benzyl-L-proline with ethyl alcohol. N-BENZYL-L-PROLINE ETHYL ESTER has been investigated for its potential pharmacological activities, including its use as a chiral building block in organic synthesis and as a precursor in the preparation of proline-containing peptides and drugs. N-Benzyl-L-proline ethyl ester has also been studied for its potential therapeutic applications, such as its ability to inhibit enzymes and as an anti-inflammatory and neuroprotective agent. Further research is needed to fully understand the potential uses and applications of this compound.

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

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

Downstream Products

• 118970-94-8 (S)-(-)-1-benzyl-2-(1-hydroxy-1-butylpentyl)-pyrrolidine 
• 151265-01-9 (S)-1-benzyl-pyrrolidine-2-carboxylic acid methylamide 
• 64-17-5 ethanol 
• 31795-93-4 N-benzyl-L-proline 
• 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 
• 1383720-79-3 (2S)-1-benzyl-N'-(cyclohexylidene)pyrrolidine-2-carbohydrazide 
• 1383720-80-6 (2S)-N-(2-adamantylidene)-1-benzylpyrrolidine-2-carbohydrazide 
• 155264-69-0 (2S)-N'-[(E)-(4-methoxyphenyl)methylidene]pyrrolidine-2-carbohydrazide 
• 1383720-81-7 (2S)-N'-[(E)-(4-nitrophenyl)methylidene]pyrrolidine-2-carbohydrazide 
• 1383720-83-9 (2S)-N'-(cyclohexylidene)pyrrolidine-2-carbohydrazide 
• 1383720-85-1 (3R,7aS)-3-(4-methoxyphenyl)-2-{[(E)-(4-methoxyphenyl)methyliden]amino}hexahydro-1H-pyrrolo[1,2-c]imidazol-1-one 
• 1383720-86-2 (3R,7aS)-3-(4-nitrophenyl)-2-{[(E)-(4-nitrophenyl)methyliden]amino}hexahydro-1H-pyrrolo[1,2-c]imidazol-1-one 
• 1383720-88-4 1-({[(2S)-1-benzylpyrrolidine-2-yl]carbonyl}amino)-3-butylurea 

Relevant articles and documents

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.