3-ethyl-6-(4-methoxyphenyl)-2-oxo-3-phenyl-1-(toluene-4-sulfonyl)-1,2,3,4-tetrahydropyridine-4-carboxylic acid ethyl ester

Base Information

• Chemical Name: 3-ethyl-6-(4-methoxyphenyl)-2-oxo-3-phenyl-1-(toluene-4-sulfonyl)-1,2,3,4-tetrahydropyridine-4-carboxylic acid ethyl ester
• CAS No.: 1276577-65-1
• Molecular Formula: C₃₀H₃₁NO₆S
• Molecular Weight: 533.645
• Mol file: 1276577-65-1.mol

Synonyms:

Chemical Property of 3-ethyl-6-(4-methoxyphenyl)-2-oxo-3-phenyl-1-(toluene-4-sulfonyl)-1,2,3,4-tetrahydropyridine-4-carboxylic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-ethyl-6-(4-methoxyphenyl)-2-oxo-3-phenyl-1-(toluene-4-sulfonyl)-1,2,3,4-tetrahydropyridine-4-carboxylic acid ethyl ester

There total 3 articles about 3-ethyl-6-(4-methoxyphenyl)-2-oxo-3-phenyl-1-(toluene-4-sulfonyl)-1,2,3,4-tetrahydropyridine-4-carboxylic acid ethyl ester 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:

phenylethylketene (20452-67-9) + 4-(4-methoxyphenyl)-4-(toluene-4-sulfonylimino)but-2-enoic acid ethyl ester (1219693-41-0) → 3-ethyl-6-(4-methoxyphenyl)-2-oxo-3-phenyl-1-(toluene-4-sulfonyl)-1,2,3,4-tetrahydropyridine-4-carboxylic acid ethyl ester (1276577-65-1) + 3-ethyl-6-(4-methoxyphenyl)-2-oxo-3-phenyl-1-(toluene-4-sulfonyl)-1,2,3,4-tetrahydropyridine-4-carboxylic acid ethyl ester

Guidance literature:

phenylethylketene; 4-(4-methoxyphenyl)-4-(toluene-4-sulfonylimino)but-2-enoic acid ethyl ester; With (5aR,10bS)-2-phenyl-4,5a,6,10b-tetrahydroindeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]-oxazin-2-ium tetrafluoroborate; caesium carbonate; In benzene; at 20 ℃; for 13h; Inert atmosphere;

In 1,2-dimethoxyethane; benzene; at 20 ℃; for 24h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1039/c0cc04839a

Reference yield:

4-(4-methoxy-phenyl)-4-oxo-crotonic acid ethyl ester (127427-28-5,39644-74-1) → 3-ethyl-6-(4-methoxyphenyl)-2-oxo-3-phenyl-1-(toluene-4-sulfonyl)-1,2,3,4-tetrahydropyridine-4-carboxylic acid ethyl ester (1276577-65-1) + 3-ethyl-6-(4-methoxyphenyl)-2-oxo-3-phenyl-1-(toluene-4-sulfonyl)-1,2,3,4-tetrahydropyridine-4-carboxylic acid ethyl ester

Guidance literature:

Multi-step reaction with 2 steps

1.1: titanium tetrachloride; triethylamine / dichloromethane / 0 °C / Reflux; Inert atmosphere

2.1: (5aR,10bS)-2-phenyl-4,5a,6,10b-tetrahydroindeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]-oxazin-2-ium tetrafluoroborate; caesium carbonate / benzene / 13 h / 20 °C / Inert atmosphere

2.2: 24 h / 20 °C / Inert atmosphere

With (5aR,10bS)-2-phenyl-4,5a,6,10b-tetrahydroindeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]-oxazin-2-ium tetrafluoroborate; titanium tetrachloride; caesium carbonate; triethylamine; In dichloromethane; benzene; 2.1: Diels-Alder reaction;

DOI:10.1039/c0cc04839a

Reference yield:

toluene-4-sulfonamide (70-55-3) → 3-ethyl-6-(4-methoxyphenyl)-2-oxo-3-phenyl-1-(toluene-4-sulfonyl)-1,2,3,4-tetrahydropyridine-4-carboxylic acid ethyl ester (1276577-65-1) + 3-ethyl-6-(4-methoxyphenyl)-2-oxo-3-phenyl-1-(toluene-4-sulfonyl)-1,2,3,4-tetrahydropyridine-4-carboxylic acid ethyl ester

Guidance literature:

Multi-step reaction with 2 steps

1.1: titanium tetrachloride; triethylamine / dichloromethane / 0 °C / Reflux; Inert atmosphere

2.1: (5aR,10bS)-2-phenyl-4,5a,6,10b-tetrahydroindeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]-oxazin-2-ium tetrafluoroborate; caesium carbonate / benzene / 13 h / 20 °C / Inert atmosphere

2.2: 24 h / 20 °C / Inert atmosphere

With (5aR,10bS)-2-phenyl-4,5a,6,10b-tetrahydroindeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]-oxazin-2-ium tetrafluoroborate; titanium tetrachloride; caesium carbonate; triethylamine; In dichloromethane; benzene; 2.1: Diels-Alder reaction;

DOI:10.1039/c0cc04839a

upstream raw materials:

phenylethylketene

4-(4-methoxyphenyl)-4-(toluene-4-sulfonylimino)but-2-enoic acid ethyl ester

4-(4-methoxy-phenyl)-4-oxo-crotonic acid ethyl ester

toluene-4-sulfonamide