Technology Process of 3-((3S,6S)-6-cyclohexyl-3-hydroxy-2-oxopiperidin-1-yl)-5-(3,3-dimethylbut-1-ynyl)thiophene-2-carboxylic acid
There total 10 articles about 3-((3S,6S)-6-cyclohexyl-3-hydroxy-2-oxopiperidin-1-yl)-5-(3,3-dimethylbut-1-ynyl)thiophene-2-carboxylic acid which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
3-((3S,6S)-6-cyclohexyl-3-hydroxy-2-oxopiperidin-1-yl)-5-(3,3-dimethylbut-1-ynyl)thiophene-2-carboxylic acid methyl ester;
With
lithium hydroxide monohydrate; water;
In
tetrahydrofuran; methanol;
at 20 - 50 ℃;
With
hydrogenchloride;
In
tetrahydrofuran; methanol; water;
pH=5;
- Guidance literature:
-
Multi-step reaction with 6 steps
1.1: triethylamine; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; copper(l) iodide / tris-(dibenzylideneacetone)dipalladium(0) / N,N-dimethyl-formamide / 48 h / 70 °C / Inert atmosphere; Sealed
1.2: pH 4
2.1: n-butyllithium / n-heptane; tetrahydrofuran / 1 h / -78 °C
2.2: 2 h / -78 - 20 °C
3.1: potassium carbonate / N,N-dimethyl-formamide / 18 h / 20 °C
4.1: potassium carbonate; copper(l) iodide / 1,4-dioxane / 48 h / 110 °C / Inert atmosphere
5.1: sodium hexamethyldisilazane / tetrahydrofuran / 1.5 h / -78 °C
5.2: 3 h / -78 °C
6.1: water; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 20 - 50 °C
6.2: pH 5
With
copper(l) iodide; n-butyllithium; lithium hydroxide monohydrate; water; sodium hexamethyldisilazane; potassium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; triethylamine;
tris-(dibenzylideneacetone)dipalladium(0);
In
tetrahydrofuran; 1,4-dioxane; methanol; n-heptane; N,N-dimethyl-formamide;
- Guidance literature:
-
Multi-step reaction with 5 steps
1.1: triethylamine; titanium tetrachloride / dichloromethane / Cooling with ice
1.2: 2.02 h / Reflux
2.1: ammonium formate / palladium 10% on activated carbon / methanol / 2 h / Reflux
3.1: potassium carbonate; copper(l) iodide / 1,4-dioxane / 48 h / 110 °C / Inert atmosphere
4.1: sodium hexamethyldisilazane / tetrahydrofuran / 1.5 h / -78 °C
4.2: 3 h / -78 °C
5.1: water; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 20 - 50 °C
5.2: pH 5
With
copper(l) iodide; lithium hydroxide monohydrate; water; ammonium formate; sodium hexamethyldisilazane; titanium tetrachloride; potassium carbonate; triethylamine;
palladium 10% on activated carbon;
In
tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane;
