Multi-step reaction with 10 steps
1.1: methanol / 4 h / 80 °C
2.1: nitric acid / 1,4-dioxane / 0.75 h / 75 - 80 °C
3.1: ammonia; hydrogen / methanol; water / 5 h / 40 °C / 3750.38 Torr / Sealed tube
4.1: diisobutylaluminium hydride / toluene / -78 - 0 °C
4.2: 0 - 20 °C
5.1: sodium hydroxide / water; ethyl acetate; acetone; toluene / 0.5 h / 20 °C
6.1: triethylamine / tetrahydrofuran / 0.5 h / 0 °C
7.1: tetrabutyl ammonium fluoride / tetrahydrofuran; acetonitrile / 1 h / 20 °C
8.1: hydrogenchloride; water / 20 h / 90 °C
9.1: sodium hydroxide / water / pH 8
9.2: 1 h / 20 °C
10.1: HATU / N,N-dimethyl-formamide / 20 °C
With
hydrogenchloride; tetrabutyl ammonium fluoride; ammonia; water; hydrogen; nitric acid; diisobutylaluminium hydride; triethylamine; HATU; sodium hydroxide;
In
tetrahydrofuran; 1,4-dioxane; methanol; water; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; acetonitrile;
DOI:10.1016/j.bmc.2010.11.038