Multi-step reaction with 8 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; potassium borohydride / Tetraethylene glycol dimethyl ether; ethanol / 0.92 h / 20 - 35 °C / Cooling with ice
2.2: 1.17 h / 20 °C / Cooling with ice
3.1: Dess-Martin periodane / dichloromethane / 2.33 h / Cooling with ice; Inert atmosphere
4.1: hydroxylamine hydrochloride; pyridine / methanol / 1 h / 20 °C
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 / 4 h / 20 °C
8.1: hydrogenchloride / water; tetrahydrofuran / 6 h / 65 - 70 °C
8.2: pH 4.6
With
pyridine; hydrogenchloride; potassium borohydride; tributylphosphine; diamide; hydroxylamine hydrochloride; hydrogen; sodium hydride; Dess-Martin periodane; triethylamine; calcium chloride;
palladium 10% on activated carbon;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; Tetraethylene glycol dimethyl ether; water; N,N-dimethyl-formamide; mineral oil;