172478-10-3

Basic information

• Product Name: N-BENZYL-D-PROLINE ETHYL ESTER
• Synonyms: N-BENZYL-D-PROLINE ETHYL ESTER;1-Benzyl-D-proline ethyl ester;N-Benzyl-D-proline ethyl ester;(R)-Ethyl 1-benzylpyrrolidine-2-carboxylate
• CAS NO: 172478-10-3
• Molecular Formula: C14H19NO2
• Molecular Weight: 233.31
• Product Categories: Amino Acid Derivatives;Peptide Synthesis;Proline
• Mol File: 172478-10-3.mol

Chemical Properties

• Boiling Point: 308.9 °C at 760 mmHg
• Flash Point: >230 °F
• Appearance: /
• Density: 1.046 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.000662mmHg at 25°C
• Refractive Index: n20/D 1.511(lit.)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: N-BENZYL-D-PROLINE ETHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: N-BENZYL-D-PROLINE ETHYL ESTER(172478-10-3)
• EPA Substance Registry System: N-BENZYL-D-PROLINE ETHYL ESTER(172478-10-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39-36
• WGK Germany: 3
• F: 34
• Hazardous Substances Data: 172478-10-3(Hazardous Substances Data)

Usage

Uses

Used in Medicinal Chemistry:
N-BENZYL-D-PROLINE ETHYL ESTER is used as a building block for the synthesis of biologically active molecules, contributing to the advancement of pharmaceuticals. Its distinctive structure enables targeted interactions with biological systems, facilitating the creation of new therapeutic agents.
Used in Drug Development:
In the pharmaceutical industry, N-BENZYL-D-PROLINE ETHYL ESTER is employed as a key component in the design and development of innovative drugs. Its potential to engage with biological targets in specific ways aids researchers in formulating more effective treatments and medicines.

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-/m1/s1

Upstream product

• 623-73-4 diazoacetic acid ethyl ester 
• 7730-39-4 N-benzyl azetidine 
• 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 
• 147-85-3 L-proline 
• 172223-83-5 5-(Benzyl-hydroxy-amino)-pentanoic acid ethyl ester 
• 622-30-0 N-benzyl hydroxylalmine 
• 14660-52-7 ethyl 5-bromovalerate 
• 172223-90-4 C₂₆H₃₀NO₄P 
• 64-17-5 ethanol 
• 31795-93-4 N-benzyl-L-proline 

Downstream Products

• 5817-26-5 ethyl (2S)-pyrrolidine-2-carboxylate 

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.

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.

One-carbon ring expansion of azetidines via ammonium ylide [1,2]-shifts: A simple route to substituted pyrrolidines

Simple N-substituted azetidines were heated with diazocarbonyl compounds in the presence of catalytic Cu(acac)2 to furnish substituted pyrrolidines via Stevens [1,2]-shift. In all but two examples, complete selectivity was seen for ring expansion rather than migration of the other exocyclic group on the azetidinium nitrogen. The two exceptions, observed with ylides substituted with two carbonyl groups and lacking a stabilizing group at the 2-position of the azetidine, underwent exocyclic benzyl migration in preference to ring expansion.

Intramolecular Nucleophilic Substitution on Nitrogen A New Heterocyclic Synthesis

A series of 5-(diphenylphosphinyloxyamino)valeric acid esters has been prepared.Their treatment with appropriate bases led to cyclization to proline derivatives.The reaction constitutes the first reported case of intramolecular nucleophilic substitution o

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.