Multi-step reaction with 18 steps
1.1: formic acid; triethylamine / 12 h / Reflux
2.1: pivaloyl chloride; triethylamine / tetrahydrofuran / 0.67 h / -10 °C
3.1: lithium chloride / tetrahydrofuran / 12 h / 20 °C
4.1: potassium hexamethylsilazane / tetrahydrofuran / 0.5 h / -78 °C
4.2: -78 °C
4.3: 16 h / -78 - 27 °C
5.1: dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; water / 3 h / 0 °C
6.1: hydrogen; palladium 10% on activated carbon / water / 12 h / 20 °C / 760.05 Torr
7.1: acetic acid; hydrogen bromide / 4 h / Reflux
8.1: acetyl chloride / 4 h / 0 °C / Reflux
9.1: sodium hydrogencarbonate / methanol; water / 3 h / 0 - 20 °C
10.1: pyridine / 2 h / 0 - 20 °C
11.1: tri-tert-butyl phosphine; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine / acetonitrile; hexane / 4 h / Inert atmosphere; Reflux
12.1: sodium hydroxide; water / tetrahydrofuran; methanol / 1 h / 20 °C
13.1: 4-methyl-morpholine; isobutyl chloroformate / tetrahydrofuran / 1 h / 0 °C
14.1: ammonia / methanol / 3 h / 0 - 20 °C
15.1: hydrogen; palladium 10% on activated carbon / ethanol / 16 h / 20 °C / 760.05 Torr
16.1: sodium carbonate / methanol; water / 2 h / 0 - 20 °C
17.1: hydrogenchloride / 1,4-dioxane / 4 h / 20 °C
18.1: acetic acid; sodium cyanoborohydride / methanol / 2.2 h / 20 °C
With
4-methyl-morpholine; pyridine; hydrogenchloride; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); formic acid; 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; isobutyl chloroformate;
In
tetrahydrofuran; 1,4-dioxane; methanol; ethanol; hexane; water; acetonitrile;