Multi-step reaction with 13 steps
1.1: N-iodo-succinimide; water / dimethyl sulfoxide / 3.5 h / 20 °C
2.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / toluene / 2 h / 100 °C
3.1: hydrogen; hydrogenchloride; 20% palladium hydroxide-activated charcoal / ethanol; 1,4-dioxane / 2 h
4.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 1 h / 20 °C
5.1: pyridine / tetrahydrofuran / 3 h / 0 - 20 °C
6.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / toluene / 1 h / 100 °C
7.1: lithium borohydride / tetrahydrofuran / 112 h / 0 - 20 °C
8.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 1.5 h / 0 - 20 °C
9.1: hydrazine hydrate / ethanol / 1.5 h / 20 - 70 °C
10.1: sodium hydrogencarbonate / ethanol; water / 1 h / 20 °C
11.1: hydrogenchloride / dichloromethane; 1,4-dioxane / 1.5 h / 20 °C
11.2: 2 h / 100 °C
12.1: potassium hydroxide; methanol / tetrahydrofuran / 0.5 h / 20 °C
13.1: N-ethyl-N,N-diisopropylamine; HATU / dichloromethane / 0.5 h / 20 °C
With
pyridine; hydrogenchloride; methanol; N-iodo-succinimide; lithium borohydride; 2,2'-azobis(isobutyronitrile); di-isopropyl azodicarboxylate; 20% palladium hydroxide-activated charcoal; water; hydrogen; tri-n-butyl-tin hydride; sodium hydrogencarbonate; hydrazine hydrate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; HATU; potassium hydroxide;
In
tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; water; dimethyl sulfoxide; toluene;