Multi-step reaction with 11 steps
1.1: triethylamine / tetrahydrofuran
2.1: triethylamine / dichloromethane
3.1: sodium azide / N,N-dimethyl-formamide / 60 °C
4.1: hydrogenchloride; methanol
5.1: triethylamine / dichloromethane
6.1: triphenylphosphine / tetrahydrofuran / 8 h / Reflux
6.2: 16 h / Reflux
7.1: triethylamine / dichloromethane / 24 h / 20 °C
8.1: palladium 10% on activated carbon; hydrogen / 1,4-dioxane / 24 h
9.1: benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine / dichloromethane / 24 h
10.1: hydrogenchloride; methanol / 1 h / 20 °C
11.1: triethylamine / dichloromethane / 24 h / 0 - 20 °C
With
hydrogenchloride; methanol; sodium azide; palladium 10% on activated carbon; hydrogen; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; triphenylphosphine;
In
tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1039/c2ob25693b