Technology Process of (S)-3-[1-(toluene-4-sulfonyl)-1H-indol-7-yl]butan-1-ol
There total 3 articles about (S)-3-[1-(toluene-4-sulfonyl)-1H-indol-7-yl]butan-1-ol which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
(S)-7-(2-but-3-enyl)-1-(toluene-4-sulfonyl)-1H-indole;
With
9-bora-bicyclo[3.3.1]nonane;
In
tetrahydrofuran;
at 0 - 20 ℃;
for 1.5h;
Inert atmosphere;
With
dihydrogen peroxide; sodium hydroxide;
In
tetrahydrofuran;
at 0 - 20 ℃;
for 0.5h;
Inert atmosphere;
DOI:10.1021/ja3004733
- Guidance literature:
-
Multi-step reaction with 4 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / toluene / 2 h / Inert atmosphere; Reflux
2.1: bi(allylnickel bromide); (R)-2,2'-binaphthoyl-benzyl-(S)-[1-(1-naphthylethyl)]aminoylphosphine; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate / dichloromethane / 3.03 h / -78 °C / 760.05 Torr
3.1: 18-crown-6 ether; potassium hydride / 1,2-dimethoxyethane / 0.5 h / 0 - 20 °C / Inert atmosphere
3.2: 14 h / 0 - 20 °C / Inert atmosphere
4.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 1.5 h / 0 - 20 °C / Inert atmosphere
4.2: 0.5 h / 0 - 20 °C / Inert atmosphere
With
tetrakis(triphenylphosphine) palladium(0); 18-crown-6 ether; bi(allylnickel bromide); (R)-2,2'-binaphthoyl-benzyl-(S)-[1-(1-naphthylethyl)]aminoylphosphine; potassium hydride; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate; 9-bora-bicyclo[3.3.1]nonane;
In
tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; toluene;
1.1: Stille coupling;
DOI:10.1021/ja3004733
- Guidance literature:
-
Multi-step reaction with 3 steps
1.1: bi(allylnickel bromide); (R)-2,2'-binaphthoyl-benzyl-(S)-[1-(1-naphthylethyl)]aminoylphosphine; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate / dichloromethane / 3.03 h / -78 °C / 760.05 Torr
2.1: 18-crown-6 ether; potassium hydride / 1,2-dimethoxyethane / 0.5 h / 0 - 20 °C / Inert atmosphere
2.2: 14 h / 0 - 20 °C / Inert atmosphere
3.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 1.5 h / 0 - 20 °C / Inert atmosphere
3.2: 0.5 h / 0 - 20 °C / Inert atmosphere
With
18-crown-6 ether; bi(allylnickel bromide); (R)-2,2'-binaphthoyl-benzyl-(S)-[1-(1-naphthylethyl)]aminoylphosphine; potassium hydride; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate; 9-bora-bicyclo[3.3.1]nonane;
In
tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane;
DOI:10.1021/ja3004733
