Multi-step reaction with 10 steps
1.1: sodium hydroxide; iodine / water / 2 h / 120 °C
2.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 15 h / -40 - 35 °C
3.1: caesium carbonate / 1,10-Phenanthroline; copper(l) iodide / toluene / 120 h / 110 °C
4.1: hydrogen / palladium on activated charcoal / ethyl acetate / 1 h
5.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 35 °C / Cooling with ice
6.1: sodium hydroxide; water / ethanol / 0.5 h / 10 - 35 °C
7.1: Dess-Martin periodane / dichloromethane / 1 h / 35 °C / Cooling with ice
8.1: 2-methyl-but-2-ene; sodium chlorite; sodium dihydrogenphosphate / water; acetone / 1 h / 10 - 35 °C
9.1: N-ethyl-N,N-diisopropylamine; HATU / dichloromethane; N,N-dimethyl-formamide / 10 - 90 °C
10.1: hydrogenchloride; water / ethanol / 0.5 h / 90 °C
10.2: 10 - 35 °C
With
hydrogenchloride; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; di-isopropyl azodicarboxylate; water; hydrogen; iodine; caesium carbonate; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; triphenylphosphine; HATU; sodium hydroxide;
copper(l) iodide; 1,10-Phenanthroline; palladium on activated charcoal;
In
tetrahydrofuran; ethanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene;
5.1: Mitsunobu reaction;