Multi-step reaction with 11 steps
1.1: nitronium tetrafluoborate / 1,2-dimethoxyethane / 4 h / -55 - -10 °C
2.1: hydrogen / palladium 10% on activated carbon / ethanol; ethyl acetate / 5 h / 1140.08 Torr
3.1: tetrahydrofuran / 16 h / Heating / reflux
4.1: sodium hydroxide; water / ethanol / 1.5 h / Heating / reflux
5.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.17 h
5.2: 20 °C
6.1: sodium hydride / N,N-dimethyl-formamide / 1.5 h
6.2: 5 - 20 °C
7.1: hydrogenchloride / 1,4-dioxane; iso-butanol / 1 h / 90 °C
8.1: hydrazine / ethanol / 16 h / 20 °C
9.1: sodium cyanoborohydride / acetic acid / methanol
10.1: hydrogen / nickel / methanol; ethanol / 2 h / 20 °C / 1292.09 Torr
11.1: acetic acid / methanol
11.2: 2 h / 0 - 20 °C
With
hydrogenchloride; dmap; sodium hydroxide; nitronium tetrafluoborate; water; hydrogen; sodium hydride; sodium cyanoborohydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; hydrazine;
palladium 10% on activated carbon; nickel; acetic acid;
In
tetrahydrofuran; 1,4-dioxane; methanol; 1,2-dimethoxyethane; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; iso-butanol;