Multi-step reaction with 11 steps
1.1: bis-triphenylphosphine-palladium(II) chloride / tetrahydrofuran / 0 °C
2.1: lithium hydroxide monohydrate; water / 1,4-dioxane / 1 h / 50 °C
2.2: 20 °C
2.3: 0.5 h
3.1: iodine; magnesium; lithium chloride / tetrahydrofuran / 50 °C
3.2: 0 - 20 °C
4.1: sodium carbonate / N,N-dimethyl-formamide
5.1: hydrogen / palladium hydroxide, 20 wt% on carbon / ethanol / 72 h / 760.05 Torr
6.1: Chiralpak.(R). AD / methanol / Resolution of racemate
7.1: caesium carbonate; potassium iodide / N,N-dimethyl-formamide
8.1: lithium hydroxide monohydrate; water / 1,4-dioxane / 1 h / 55 °C
8.2: 20 °C
9.1: triethylamine; isobutyl chloroformate / acetone / 1 h / 20 °C
9.2: 0 °C
9.3: Reflux
10.1: hydrogenchloride; water / 1,4-dioxane / 0 - 20 °C
11.1: sodium azide; acetic acid / 95 °C
With
hydrogenchloride; sodium azide; lithium hydroxide monohydrate; water; hydrogen; iodine; sodium carbonate; caesium carbonate; magnesium; acetic acid; triethylamine; potassium iodide; lithium chloride; isobutyl chloroformate;
bis-triphenylphosphine-palladium(II) chloride; palladium hydroxide, 20 wt% on carbon;
In
tetrahydrofuran; 1,4-dioxane; methanol; ethanol; N,N-dimethyl-formamide; acetone;