108634-46-4

Basic information

• Product Name: 1-benzyl-5-ethoxypyrrolidin-2-one
• CAS NO: 108634-46-4
• Molecular Formula: C₁₃H₁₇NO₂
• Molecular Weight: 219.2796
• Mol File: 108634-46-4.mol

Chemical Properties

• Boiling Point: 377.2°C at 760 mmHg
• Flash Point: 181.9°C
• Density: 1.11g/cm³
• Vapor Pressure: 6.85E-06mmHg at 25°C
• Refractive Index: 1.551
• CAS DataBase Reference: 1-benzyl-5-ethoxypyrrolidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-benzyl-5-ethoxypyrrolidin-2-one(108634-46-4)
• EPA Substance Registry System: 1-benzyl-5-ethoxypyrrolidin-2-one(108634-46-4)

Safety Data

• Hazardous Substances Data: 108634-46-4(Hazardous Substances Data)

Upstream product

• 2142-06-5 1-(phenylmethyl)-2,5-pyrrolidinedione 
• 64-17-5 ethanol 
• 39662-63-0 5-ethoxy-pyrrolidin-2-one 
• 100-39-0 benzyl bromide 
• 96-48-0 4-butanolide 
• 100-46-9 benzylamine 

Downstream Products

• 88996-11-6 (1R,4R,5R)-6-Benzyl-4-vinyl-6-aza-bicyclo[3.2.1]octan-7-one 
• 88996-11-6 (1R,4S,5R)-6-Benzyl-4-vinyl-6-aza-bicyclo[3.2.1]octan-7-one 
• 88996-19-4 1-Benzyl-3-pent-4-enyl-1,5-dihydro-pyrrol-2-one 
• 88996-10-5 6-benzyl-4-vinylidene-6-azabicyclo<3.2.1>octan-7-one 
• 121823-51-6 1-benzyl-5-ethoxy-3-<4-(trimethylsilyl)-2-butynyl>-2-pyrrolidinone 

Relevant articles and documents

Microbial decyanation of 1-benzylpyrrolidine-2,5-dicarbonitrile. Mechanistic investigations

Various bacterial and fungal strains were screened for their ability to catalyse the regioselective hydrolysis of 1-benzylpyrrolidine-2,5-dicarbonitrile (1). Among the examined strains, Rhodococcus opacus sp-lma whole cells transformed both isomers of 1 into 1-benzyl-5-cyano-2-pyrrolidinone (2) and N-benzylacetamide (3). These reactions are difficult to achieve chemically and the synthesis of compound 2 did not compete with microbiological catalysis in terms of efficiency and respect for the guidelines of green chemistry. To distinguish between an oxidative or hydrolytic based-mechanism, the origin of the oxygen atom in 2 was investigated by using 18O2 and 18OH2 coupled with GC-MS analysis. These experiments confirmed that the oxygen atom in 2 came from water and not from molecular oxygen. The reaction is probably initiated by the dehydrogenation of 1 to generate the iminium ion, which could be trapped by a water molecule to form the cyanohydrin. The cyanohydrin intermediate would spontaneously break down to the γ-lactam product 2. Conversion of 1 to 2 by induced rat liver microsomes suggests the involvement of a Cyt P-450-type enzyme. A mechanism that accounts for the formation of 3 is also proposed.

Influence of N-substituted lactams on acyclic free radical based hydrogen transfer

anti Relative stereochemistry is achieved in the hydrogen-transfer reaction of a lactam adjacent to the carbon-centered radical. The sense of diastereoselectivity is reversed using N-substituted lactams, and optimal results favoring syn reduced products are obtained with an α-methylbenzyl group and a Boc group.

Acyliminium Ion Cyclisations to Pyrrolo- and Pyrido-phenanthridine and Benzopyrroloisoquinoline Ring Systems

Pyrrolo- and pyrido-phenanthridines and benzopyrroloisoquinolines are obtained by acid-catalysed cyclodehydration of appropriate hydroxy lactams and keto amides derived from N-substituted succinimide and glutarimide derivatives.

Amnesia-reversal activity of a series of 5-alkoxy-1-arylcarbonyl-2-pyrrolidinones and 5-alkoxy-1-arylmethyl-2-pyrrolidinones

A series of 5-alkoxy-1-arylcarbonyl-2-pyrrolidinones (1-27) were prepared by condensation of arylcarbonyl chlorides with 5-alkoxy-2-pyrrolidinones in the presence of butyl lithium in tetrahydrofuran.Alkylation of these intermediates with substituted benzy

Substitution reactions of 2-phenylsulphonyl-piperidines and -pyrrolidines with carbon nucleophiles: Synthesis of the pyrrolidine alkaloids norruspoline and ruspolinone

Several 2-phenylsulphonyl-piperidines and -pyrrolidines were prepared from the corresponding N-acyl aminals by treatment with benzenesulphinic acid. On reaction with various carbon nucleophiles these sulphones gave good yields of substitution products. Typical nucleophiles used in these studies were organometallic reagents derived from Grignard reagents and zinc halide together with silyl enol ethers, silyl ketene acetals, allylsilanes and trimethylsilyl cyanide in the presence of a Lewis acid. These methods were employed in the synthesis of two natural product alkaloids; Norruspoline (38) and Ruspolinone (40).

A novel synthetic route to 6-azabicyclooct-3-enes via silicon directed N-acyliminium chemistry. Synthesis of (+/-)-gabaculine

Alkylation of the lithium enolate, derived from 5-ethoxy-2-pyrrolidone 1 (Scheme 1), using alkyl halides containing either the vinylsilane or 2-propynylsilane moiety, provides substrates 3 for cyclization studies passing through N-acyliminium intermediate

ω-Alkoxy Lactams as Dipolar Synthons. Silicon-Assisted Synthesis of Azabicycles and a γ-Amino Acid

Alkylation of the lithium enolates derived from ω-alkoxy lactams 1a-c with unsaturated iodides 4 affords 5 in high yields (Table I).Those alkylation products 5, which contain an allyl- or propargylsilane moiety, undergo cyclization on acid treatment to fu