diethyl 4-(trichloromethylcarbonylamino)-1,2,3,4-tetrahydro-2-(p-toluenesulfonyl)isoquinoline-5,6-dicarboxylate

Base Information

• Chemical Name: diethyl 4-(trichloromethylcarbonylamino)-1,2,3,4-tetrahydro-2-(p-toluenesulfonyl)isoquinoline-5,6-dicarboxylate
• CAS No.: 1446089-48-0
• Molecular Formula: C₂₄H₂₅Cl₃N₂O₇S
• Molecular Weight: 591.897

Synonyms:

Chemical Property of diethyl 4-(trichloromethylcarbonylamino)-1,2,3,4-tetrahydro-2-(p-toluenesulfonyl)isoquinoline-5,6-dicarboxylate

Chemical Property:

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Technology Process of diethyl 4-(trichloromethylcarbonylamino)-1,2,3,4-tetrahydro-2-(p-toluenesulfonyl)isoquinoline-5,6-dicarboxylate

There total 8 articles about diethyl 4-(trichloromethylcarbonylamino)-1,2,3,4-tetrahydro-2-(p-toluenesulfonyl)isoquinoline-5,6-dicarboxylate 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:

C24H27Cl3N2O7S → diethyl 4-(trichloromethylcarbonylamino)-1,2,3,4-tetrahydro-2-(p-toluenesulfonyl)isoquinoline-5,6-dicarboxylate (1446089-48-0)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In toluene; at 115 ℃; for 2h; Inert atmosphere; Sealed tube; Microwave irradiation;

DOI:10.1021/jo401182r

Reference yield:

3-(trichloromethylcarbonylamino)-1,2,3,6-tetrahydro-1-(p-toluenesulfonyl)-5-ethyl-1-enepyridine (1446089-44-6) → diethyl 4-(trichloromethylcarbonylamino)-1,2,3,4-tetrahydro-2-(p-toluenesulfonyl)isoquinoline-5,6-dicarboxylate (1446089-48-0)

Guidance literature:

Multi-step reaction with 2 steps

1: hydroquinone; zinc(II) chloride / toluene / 3 h / 140 °C / Inert atmosphere; Sealed tube; Microwave irradiation

2: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 2 h / 115 °C / Inert atmosphere; Sealed tube; Microwave irradiation

With hydroquinone; 2,3-dicyano-5,6-dichloro-p-benzoquinone; zinc(II) chloride; In toluene; 1: |Diels-Alder Cycloaddition;

DOI:10.1021/jo401182r

Reference yield:

N-(2-hydroxyethyl)-4-methyl-N-(prop-2-yn-1-yl)benzenesulfonamide (317842-46-9) → diethyl 4-(trichloromethylcarbonylamino)-1,2,3,4-tetrahydro-2-(p-toluenesulfonyl)isoquinoline-5,6-dicarboxylate (1446089-48-0)

Guidance literature:

Multi-step reaction with 8 steps

1.1: dimethyl sulfoxide; triethylamine / dichloromethane / -78 - 20 °C / Inert atmosphere

1.2: 3.5 h / -78 - 20 °C / Inert atmosphere

2.1: lithium chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 1 h / Inert atmosphere

2.2: 20 °C / Inert atmosphere

3.1: diisobutylaluminium hydride / diethyl ether / -78 - 20 °C / Inert atmosphere

4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere

5.1: potassium carbonate / toluene / 24 h / 140 °C / Inert atmosphere; Sealed tube

6.1: Hoveyda-Grubbs catalyst second generation / 24 h / 90 °C / Inert atmosphere

7.1: hydroquinone; zinc(II) chloride / toluene / 3 h / 140 °C / Inert atmosphere; Sealed tube; Microwave irradiation

8.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 2 h / 115 °C / Inert atmosphere; Sealed tube; Microwave irradiation

With Hoveyda-Grubbs catalyst second generation; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; hydroquinone; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium chloride; zinc(II) chloride; In diethyl ether; dichloromethane; toluene; acetonitrile; 1.1: |Swern Oxidation / 1.2: |Swern Oxidation / 2.1: |Horner-Wadsworth-Emmons Olefination / 2.2: |Horner-Wadsworth-Emmons Olefination / 7.1: |Diels-Alder Cycloaddition;

DOI:10.1021/jo401182r

upstream raw materials:

3-(trichloromethylcarbonylamino)-1,2,3,6-tetrahydro-1-(p-toluenesulfonyl)-5-ethyl-1-enepyridine

N-(2-hydroxyethyl)-4-methyl-N-(prop-2-yn-1-yl)benzenesulfonamide

4-methyl-N-(2-oxoethyl)-N-(prop-2-yn-1-yl)benzenesulfonamide

ethyl (E)-4-(N-(prop-2-ynyl)-4-methylphenylsulfonamido)but-2-enoate

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