Multi-step reaction with 19 steps
1.1: sodium hydroxide / tetrahydrofuran / 3 h / 0 - 20 °C
2.1: aluminum (III) chloride / dichloromethane / 0.17 h / 0 °C
2.2: 3 h / 0 - 20 °C
3.1: hydrogenchloride; zinc / toluene / 3 h / Reflux
4.1: pivaloyl chloride; lithium chloride; triethylamine / tetrahydrofuran / 2 h / -25 - 20 °C
5.1: potassium hexamethylsilazane / tetrahydrofuran / 0.5 h / -78 °C
5.2: -78 °C
5.3: 4 h / -78 - 27 °C
6.1: dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; water / 1 h / 0 °C
7.1: hydrogen; palladium 10% on activated carbon / water / 16 h / 20 °C / 760.05 Torr
8.1: acetic acid; hydrogen bromide / 16 h / Reflux
9.1: acetyl chloride / 3 h / Reflux
10.1: sodium hydrogencarbonate / methanol; water / 3 h / 0 - 20 °C
11.1: pyridine / 1 h / 0 - 20 °C
12.1: tri-tert-butyl phosphine; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine / acetonitrile; hexane / 16 h / Inert atmosphere; Reflux
13.1: sodium hydroxide; water / tetrahydrofuran; methanol / 1 h / 20 °C
14.1: 4-methyl-morpholine; pivaloyl chloride / tetrahydrofuran / 1 h / 0 °C
15.1: ammonia / methanol / 2 h / 0 - 20 °C
16.1: hydrogen; palladium 10% on activated carbon / ethanol / 16 h / 20 °C / 760.05 Torr
17.1: sodium carbonate / methanol; water / 2 h / 0 - 20 °C
18.1: hydrogenchloride / 1,4-dioxane / 1 h / 20 °C
19.1: acetic acid; sodium cyanoborohydride / methanol / 2.2 h / 20 °C
With
4-methyl-morpholine; pyridine; hydrogenchloride; aluminum (III) chloride; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); tri-tert-butyl phosphine; palladium 10% on activated carbon; ammonia; water; hydrogen bromide; hydrogen; dihydrogen peroxide; pivaloyl chloride; potassium hexamethylsilazane; sodium cyanoborohydride; sodium hydrogencarbonate; sodium carbonate; acetic acid; triethylamine; acetyl chloride; lithium chloride; sodium hydroxide; lithium hydroxide; zinc;
In
tetrahydrofuran; 1,4-dioxane; methanol; ethanol; hexane; dichloromethane; water; toluene; acetonitrile;