ethyl (2E)-3-[3-{[(tert-butoxycarbonyl)amino]methyl}-2-(2-methylpropyl)-1-oxo-4-phenyl-1,2-dihydroisoquinolin-6-yl]prop-2-enoate

Base Information

• Chemical Name: ethyl (2E)-3-[3-{[(tert-butoxycarbonyl)amino]methyl}-2-(2-methylpropyl)-1-oxo-4-phenyl-1,2-dihydroisoquinolin-6-yl]prop-2-enoate
• CAS No.: 447424-07-9
• Molecular Formula: C₃₀H₃₆N₂O₅
• Molecular Weight: 504.626

Synonyms:ethyl (2E)-3-[3-{[(tert-butoxycarbonyl)amino]methyl}-2-(2-methylpropyl)-1-oxo-4-phenyl-1,2-dihydroisoquinolin-6-yl]prop-2-enoate

Chemical Property of ethyl (2E)-3-[3-{[(tert-butoxycarbonyl)amino]methyl}-2-(2-methylpropyl)-1-oxo-4-phenyl-1,2-dihydroisoquinolin-6-yl]prop-2-enoate

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

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Technology Process of ethyl (2E)-3-[3-{[(tert-butoxycarbonyl)amino]methyl}-2-(2-methylpropyl)-1-oxo-4-phenyl-1,2-dihydroisoquinolin-6-yl]prop-2-enoate

There total 11 articles about ethyl (2E)-3-[3-{[(tert-butoxycarbonyl)amino]methyl}-2-(2-methylpropyl)-1-oxo-4-phenyl-1,2-dihydroisoquinolin-6-yl]prop-2-enoate 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: 90.0%

tert-butyl {[6-bromo-2-(2-methylpropyl)-1-oxo-4-phenyl-1,2-dihydroisoquinolin-3-yl]methyl}carbamate (447423-16-7) + ethyl acrylate (140-88-5,9003-32-1) → ethyl (2E)-3-[3-{[(tert-butoxycarbonyl)amino]methyl}-2-(2-methylpropyl)-1-oxo-4-phenyl-1,2-dihydroisoquinolin-6-yl]prop-2-enoate (447424-07-9)

Guidance literature:

With palladium diacetate; triethylamine; In N,N-dimethyl-formamide; at 80 ℃; for 8h; diastereoselective reaction; Inert atmosphere;

DOI:10.1016/j.bmc.2011.06.059

Reference yield:

C21H19BrO7 → ethyl (2E)-3-[3-{[(tert-butoxycarbonyl)amino]methyl}-2-(2-methylpropyl)-1-oxo-4-phenyl-1,2-dihydroisoquinolin-6-yl]prop-2-enoate (447424-07-9)

Guidance literature:

Multi-step reaction with 9 steps

1: hydrogenchloride; water; acetic acid / 8 h / 120 °C

2: methanol / 15 h / 20 °C

3: hydrogenchloride / ethyl acetate / 3 h / 20 °C

4: oxalyl dichloride; N,N-dimethyl-formamide / tetrahydrofuran / 2 h / 20 °C

5: sodium tetrahydroborate / tetrahydrofuran; 1,2-dimethoxyethane / 2 h / 0 °C

6: pyridine; thionyl chloride / tetrahydrofuran; toluene / 3 h / 20 °C

7: ammonia / tetrahydrofuran; ethanol / 5 h / 140 °C / Sealed tube

8: dmap / tetrahydrofuran / 1 h / 20 °C

9: palladium diacetate; triethylamine / N,N-dimethyl-formamide / 8 h / 80 °C / Inert atmosphere

With pyridine; hydrogenchloride; dmap; sodium tetrahydroborate; thionyl chloride; oxalyl dichloride; ammonia; water; palladium diacetate; acetic acid; triethylamine; N,N-dimethyl-formamide; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; ethanol; ethyl acetate; N,N-dimethyl-formamide; toluene; 9: Heck reaction;

DOI:10.1016/j.bmc.2011.06.059

Reference yield:

6-bromo-1-oxo-4-phenyl-1H-isochromene-3-carboxylic acid (583837-70-1) → ethyl (2E)-3-[3-{[(tert-butoxycarbonyl)amino]methyl}-2-(2-methylpropyl)-1-oxo-4-phenyl-1,2-dihydroisoquinolin-6-yl]prop-2-enoate (447424-07-9)

Guidance literature:

Multi-step reaction with 8 steps

1: methanol / 15 h / 20 °C

2: hydrogenchloride / ethyl acetate / 3 h / 20 °C

3: oxalyl dichloride; N,N-dimethyl-formamide / tetrahydrofuran / 2 h / 20 °C

4: sodium tetrahydroborate / tetrahydrofuran; 1,2-dimethoxyethane / 2 h / 0 °C

5: pyridine; thionyl chloride / tetrahydrofuran; toluene / 3 h / 20 °C

6: ammonia / tetrahydrofuran; ethanol / 5 h / 140 °C / Sealed tube

7: dmap / tetrahydrofuran / 1 h / 20 °C

8: palladium diacetate; triethylamine / N,N-dimethyl-formamide / 8 h / 80 °C / Inert atmosphere

With pyridine; hydrogenchloride; dmap; sodium tetrahydroborate; thionyl chloride; oxalyl dichloride; ammonia; palladium diacetate; triethylamine; N,N-dimethyl-formamide; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; ethanol; ethyl acetate; N,N-dimethyl-formamide; toluene; 8: Heck reaction;

DOI:10.1016/j.bmc.2011.06.059

upstream raw materials:

6-bromo-1-oxo-4-phenyl-1H-isochromene-3-carboxylic acid

6-bromo-3-(chloromethyl)-2-(2-methylpropyl)-4-phenylisoquinolin-1(2H)-one

3-(aminomethyl)-6-bromo-2-(2-methyl)propyl-4-phenylisoquinolin-1(2H)-one

6-bromo-3-(hydroxymethyl)-2-(2-methylpropyl)-4-phenylisoquinolin-1(2H)-one

Downstream raw materials:

ethyl 3-[3-{[(tert-butoxycarbonyl)amino]methyl}-2-(2-methylpropyl)-1-oxo-4-phenyl-1,2-dihydroisoquinolin-6-yl]propanoate

(2E)-3-[3-{[(tert-butoxycarbonyl)amino]methyl}-2-(2-methylpropyl)-1-oxo-4-phenyl-1,2-dihydroisoquinolin-6-yl]prop-2-enoic acid

3-[3-{[(tert-butoxycarbonyl)amino]methyl}-2-(2-methylpropyl)-1-oxo-4-phenyl-1,2-dihydroisoquinolin-6-yl]propanoic acid

tert-butyl ({6-[(1E)-3-amino-3-oxoprop-1-en-1-yl]-2-(2-methylpropyl)-1-oxo-4-phenyl-1,2-dihydroisoquinolin-3-yl}methyl)carbamate

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