Multi-step reaction with 12 steps
1.1: toluene-4-sulfonic acid / acetone / 1 h / -20 - 20 °C
1.2: 0.08 h / 20 °C
2.1: 1H-imidazole / dmap / dichloromethane / 20 °C
3.1: dimethylsulfide borane complex / tetrahydrofuran / 5 h / 0 °C
3.2: 16 h / 20 °C
4.1: triethylamine / dichloromethane / 1 h / 0 - 20 °C
5.1: tetraethylammonium fluoride / tetrahydrofuran; water / Heating / reflux
6.1: toluene-4-sulfonic acid / methanol / 12 h / 20 °C
6.2: 0.5 h
7.1: pyridine / dichloromethane / 16 h / 20 °C
8.1: sodium azide / N,N-dimethyl-formamide / 1.5 h / 80 °C
9.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C
9.2: 12 h / -78 - 0 °C
10.1: hydrogen / palladium 10% on activated carbon / ethyl acetate / 2 h / 2068.65 Torr
11.1: benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h
12.1: hydrogenchloride / 1,4-dioxane; acetonitrile
With
pyridine; 1H-imidazole; hydrogenchloride; sodium azide; dimethylsulfide borane complex; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; hydrogen; tetraethylammonium fluoride; toluene-4-sulfonic acid; triethylamine; N-ethyl-N,N-diisopropylamine; lithium hexamethyldisilazane;
dmap; palladium 10% on activated carbon;
In
tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; acetonitrile;