Multi-step reaction with 9 steps
1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1.33 h / 20 °C / Inert atmosphere; Cooling with ice
1.2: 1.17 h / 20 °C / Cooling with ice
2.1: calcium chloride / ethanol / 0.33 h / Cooling with ice
2.2: 0.58 h / 20 - 35 °C
3.1: Dess-Martin periodane / dichloromethane / 2.33 h / 20 °C / Cooling with ice; Inert atmosphere
4.1: pyridine; hydroxylamine hydrochloride / methanol; ethyl acetate
5.1: hydrogen / palladium 10% on activated carbon / ethanol; water / 1 h / 20 °C / 760.05 Torr
6.1: triethylamine / dichloromethane / 1 h / 20 °C
7.1: tributylphosphine; diamide / tetrahydrofuran / 8.5 h / 20 °C
8.1: triethylamine / dichloromethane / 3 h / 20 °C / Cooling with ice
9.1: hydrogenchloride / 1,4-dioxane; dichloromethane / 7 h / 20 °C
9.2: pH 4.7
With
pyridine; hydrogenchloride; tributylphosphine; diamide; hydroxylamine hydrochloride; hydrogen; sodium hydride; Dess-Martin periodane; triethylamine; calcium chloride;
palladium 10% on activated carbon;
In
tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; mineral oil;