Multi-step reaction with 13 steps
1.1: sodium perborate; acetic acid / 21 h / 65 - 70 °C / Inert atmosphere
2.1: 1-methyl-pyrrolidin-2-one / 6 h / 160 - 165 °C / Inert atmosphere
3.1: thionyl chloride / 0 - 25 °C / Inert atmosphere
4.1: diisobutylaluminium hydride / tetrahydrofuran; hexane / 4 h / 0 - 5 °C / Inert atmosphere
4.2: 0.5 h / 25 °C / Cooling with ice; Inert atmosphere
5.1: phosphorus tribromide / 24 h / 25 °C / Inert atmosphere
6.1: potassium carbonate / acetone / 2.5 h / 25 - 30 °C / Inert atmosphere
7.1: palladium diacetate; triethylamine; triphenylphosphine / tert-butyl methyl ether / 16 h / 25 °C / Inert atmosphere
8.1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / -70 °C / Inert atmosphere
9.1: Chiralpak AD-I / ethanol; n-heptane / Inert atmosphere
10.1: potassium peroxymonosulfate / tetrahydrofuran; water / 2 h / 40 °C / Inert atmosphere
11.1: hydrogenchloride / 1,4-dioxane / 2 h / 25 °C / Inert atmosphere
12.1: sodium acetate / methanol; dichloromethane / 0.5 h / 25 °C / Inert atmosphere
12.2: 1 h / Inert atmosphere
12.3: 0.25 h / Inert atmosphere
13.1: potassium hydroxide / tetrahydrofuran / 0.33 h / Microwave irradiation
With
1-methyl-pyrrolidin-2-one; hydrogenchloride; sodium perborate; lithium aluminium tetrahydride; thionyl chloride; potassium peroxymonosulfate; sodium acetate; palladium diacetate; phosphorus tribromide; diisobutylaluminium hydride; potassium carbonate; acetic acid; triethylamine; triphenylphosphine; potassium hydroxide;
In
tetrahydrofuran; 1,4-dioxane; methanol; ethanol; hexane; n-heptane; dichloromethane; tert-butyl methyl ether; water; acetone;
DOI:10.1021/jm300069y