methyl 4-<(tert-butyldimethylsilyl)oxy>-2-(4'-methylbenzenesulfonyl)-3-oxo-2-azabicyclo<2.2.2>oct-7-ene-5-endo-carboxylate

Base Information

• Chemical Name: methyl 4-<(tert-butyldimethylsilyl)oxy>-2-(4'-methylbenzenesulfonyl)-3-oxo-2-azabicyclo<2.2.2>oct-7-ene-5-endo-carboxylate
• CAS No.: 141667-44-9
• Molecular Formula: C₂₂H₃₁NO₆SSi
• Molecular Weight: 465.643
• Mol file: 141667-44-9.mol

Synonyms:methyl 4-<(tert-butyldimethylsilyl)oxy>-2-(4'-methylbenzenesulfonyl)-3-oxo-2-azabicyclo<2.2.2>oct-7-ene-5-endo-carboxylate

Chemical Property of methyl 4-<(tert-butyldimethylsilyl)oxy>-2-(4'-methylbenzenesulfonyl)-3-oxo-2-azabicyclo<2.2.2>oct-7-ene-5-endo-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 4-<(tert-butyldimethylsilyl)oxy>-2-(4'-methylbenzenesulfonyl)-3-oxo-2-azabicyclo<2.2.2>oct-7-ene-5-endo-carboxylate

There total 6 articles about methyl 4-<(tert-butyldimethylsilyl)oxy>-2-(4'-methylbenzenesulfonyl)-3-oxo-2-azabicyclo<2.2.2>oct-7-ene-5-endo-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: 57.0%

methanol (67-56-1) + 3-[(tert-butyl)dimethylsilyloxy]-1-[(4-methylphenyl)sulfonyl]-1H-pyridin-2-one (141667-31-4) + acryloyl chloride (814-68-6,25189-84-8) → methyl 4-<(tert-butyldimethylsilyl)oxy>-2-(4'-methylbenzenesulfonyl)-3-oxo-2-azabicyclo<2.2.2>oct-7-ene-5-endo-carboxylate (141667-44-9)

Guidance literature:

3-[(tert-butyl)dimethylsilyloxy]-1-[(4-methylphenyl)sulfonyl]-1H-pyridin-2-one; acryloyl chloride; With 2,6-di-tert-butyl-4-methyl-phenol; In dichloromethane; at 110 ℃; for 144h;

methanol; With triethylamine; In dichloromethane; at 23 ℃; for 20h;

DOI:10.1002/hlca.200390320

Reference yield: 56.0%

3-[(tert-butyl)dimethylsilyloxy]-1-[(4-methylphenyl)sulfonyl]-1H-pyridin-2-one (141667-31-4) + acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) → methyl 4-<(tert-butyldimethylsilyl)oxy>-2-(4'-methylbenzenesulfonyl)-3-oxo-2-azabicyclo<2.2.2>oct-7-ene-5-endo-carboxylate (141667-44-9)

Guidance literature:

With 2,6-di-tert-butyl-4-methyl-phenol; In dichloromethane; at 90 ℃; for 110h;

DOI:10.1021/jo00041a010

Reference yield:

dihydroxypyridine (16867-04-2) → methyl 4-<(tert-butyldimethylsilyl)oxy>-2-(4'-methylbenzenesulfonyl)-3-oxo-2-azabicyclo<2.2.2>oct-7-ene-5-endo-carboxylate (141667-44-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 70 percent / 1H-imidazole / dimethylformamide / 23 °C

2.1: MeLi / diethyl ether / 2 h / 0 °C

2.2: 82 percent / diethyl ether / 30 h / 23 °C

3.1: 23 percent / 2,6-di-(tert-butyl)-4-methylphenol / CH₂Cl₂ / 230 h / 110 °C

With 1H-imidazole; 2,6-di-tert-butyl-4-methyl-phenol; methyllithium; In diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/hlca.200390320

upstream raw materials:

3-[(tert-butyl)dimethylsilyloxy]-1-[(4-methylphenyl)sulfonyl]-1H-pyridin-2-one

acrylic acid methyl ester

methanol

acryloyl chloride