ethyl 6-(bromoacetyl)-8-(benzyloxy)-2-methyl-1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-7-carboxylate

Base Information

• Chemical Name: ethyl 6-(bromoacetyl)-8-(benzyloxy)-2-methyl-1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-7-carboxylate
• CAS No.: 870006-71-6
• Molecular Formula: C₂₀H₂₁BrN₂O₅
• Molecular Weight: 449.301
• Mol file: 870006-71-6.mol

Synonyms:ethyl 6-(bromoacetyl)-8-(benzyloxy)-2-methyl-1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-7-carboxylate

Chemical Property of ethyl 6-(bromoacetyl)-8-(benzyloxy)-2-methyl-1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-7-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 6-(bromoacetyl)-8-(benzyloxy)-2-methyl-1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-7-carboxylate

There total 9 articles about ethyl 6-(bromoacetyl)-8-(benzyloxy)-2-methyl-1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-7-carboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

ethyl 6-acetyl-8-(benzyloxy)-2-methyl-1-oxo-1,2,3,4-tetrahydro-pyrrolo[1,2-a]-pyrazine-7-carboxylate (869901-54-2) → ethyl 6-(bromoacetyl)-8-(benzyloxy)-2-methyl-1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-7-carboxylate (870006-71-6)

Guidance literature:

With hydrogen bromide; bromine; acetic acid; In chloroform; at 20 ℃; for 6h;

Reference yield:

4-benzyloxycarbonyl-1-methyl-3,4-dihydropyrazin-2(1H)-one (851726-65-3) → ethyl 6-(bromoacetyl)-8-(benzyloxy)-2-methyl-1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-7-carboxylate (870006-71-6)

Guidance literature:

Multi-step reaction with 7 steps

1.1: hydrogen / 10% Pt/activated carbon / ethanol / 20 °C / 760.05 Torr

1.2: 24 h

2.1: toluene / 100 °C

3.1: lithium hexamethyldisilazane / tetrahydrofuran / 20 °C / Heating / reflux

4.1: potassium carbonate / N,N-dimethyl-formamide / 20 °C

5.1: bromine; sodium hydrogencarbonate / dichloromethane / 2 h / 0 - 20 °C

6.1: -butyl vinyl ether; 1,3-bis-(diphenylphosphino)propane; N-ethyl-N,N-diisopropylamine / palladium diacetate / N,N-dimethyl-formamide / 100 °C

7.1: hydrogen bromide; bromine; acetic acid / chloroform / 6 h / 20 °C

With -butyl vinyl ether; 1,3-bis-(diphenylphosphino)propane; hydrogen bromide; hydrogen; bromine; sodium hydrogencarbonate; potassium carbonate; acetic acid; N-ethyl-N,N-diisopropylamine; lithium hexamethyldisilazane; palladium diacetate; 10% Pt/activated carbon; In tetrahydrofuran; ethanol; dichloromethane; chloroform; N,N-dimethyl-formamide; toluene;

Reference yield:

ethyl 8-hydroxy-2-methyl-1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]-pyrazine-7-carboxylate (701208-31-3) → ethyl 6-(bromoacetyl)-8-(benzyloxy)-2-methyl-1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-7-carboxylate (870006-71-6)

Guidance literature:

Multi-step reaction with 4 steps

1: potassium carbonate / N,N-dimethyl-formamide / 20 °C

2: bromine; sodium hydrogencarbonate / dichloromethane / 2 h / 0 - 20 °C

3: -butyl vinyl ether; 1,3-bis-(diphenylphosphino)propane; N-ethyl-N,N-diisopropylamine / palladium diacetate / N,N-dimethyl-formamide / 100 °C

4: hydrogen bromide; bromine; acetic acid / chloroform / 6 h / 20 °C

With -butyl vinyl ether; 1,3-bis-(diphenylphosphino)propane; hydrogen bromide; bromine; sodium hydrogencarbonate; potassium carbonate; acetic acid; N-ethyl-N,N-diisopropylamine; palladium diacetate; In dichloromethane; chloroform; N,N-dimethyl-formamide;

upstream raw materials:

ethyl 6-acetyl-8-(benzyloxy)-2-methyl-1-oxo-1,2,3,4-tetrahydro-pyrrolo[1,2-a]-pyrazine-7-carboxylate

4-benzyloxycarbonyl-1-methyl-3,4-dihydropyrazin-2(1H)-one

ethyl 8-hydroxy-2-methyl-1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]-pyrazine-7-carboxylate

benzyl (2-((2,2-dimethoxyethyl)(methyl)amino)-2-oxoethyl)carbamate

Downstream raw materials:

ethyl 8-(benzyloxy)-6-[(1,1-dioxido-1,2-thiazinan-2-yl)acetyl]-2-methyl-1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-7-carboxylate