Multi-step reaction with 18 steps
1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 0.25 h / 0 °C
1.2: 36 h / 20 °C
2.1: hydrogen; palladium 10% on activated carbon / ethanol / 16 h / 20 °C / 760.05 Torr
3.1: sodium hydroxide; water / tetrahydrofuran; methanol / 1 h / 20 °C
4.1: n-butyllithium / tetrahydrofuran; cyclohexane / 1 h / -78 °C
4.2: 1.8 h / -78 - 20 °C
5.1: potassium hexamethylsilazane / tetrahydrofuran / 0.5 h / -78 °C
5.2: 0.08 h / -78 °C
5.3: 16 h / -78 - 24 °C
6.1: dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; water / 1.2 h / 0 - 20 °C
7.1: hydrogen; palladium 10% on activated carbon / water / 3 h / 20 °C / 760.05 Torr
8.1: acetic acid; hydrogen bromide / 3 h / Reflux
9.1: acetyl chloride / 4 h / 0 °C / Reflux
10.1: sodium hydrogencarbonate / methanol; water / 1 h / 0 - 20 °C
11.1: pyridine / 2 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 / 2 h / 20 °C
14.1: 4-methyl-morpholine; pivaloyl chloride / tetrahydrofuran / 2 h / 0 °C
15.1: ammonia / methanol / 18 h / 0 - 20 °C
16.1: hydrogen; palladium 10% on activated carbon / ethanol / 16 h / 20 °C / 760.05 Torr
17.1: sodium hydrogencarbonate / methanol; water / 0.17 h / 0 °C
17.2: 2 h / 0 - 20 °C
18.1: hydrogenchloride / 1,4-dioxane / 1 h / 20 °C
With
4-methyl-morpholine; pyridine; hydrogenchloride; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); n-butyllithium; tri-tert-butyl phosphine; palladium 10% on activated carbon; ammonia; water; hydrogen bromide; hydrogen; dihydrogen peroxide; pivaloyl chloride; potassium hexamethylsilazane; sodium hydrogencarbonate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; acetyl chloride; sodium hydroxide; lithium hydroxide;
In
tetrahydrofuran; 1,4-dioxane; methanol; ethanol; hexane; dichloromethane; cyclohexane; water; acetonitrile;