Multi-step reaction with 16 steps
1.1: ammonium chloride; ammonia / methanol / 96 h / 20 °C
2.1: hydrogenchloride / methanol / 96 h / Reflux
2.2: 20 °C
3.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / -15 - 0 °C
4.1: sodium hydrogencarbonate / tetrahydrofuran / 15.17 h / 0 - 20 °C
5.1: Dess-Martin periodane / dichloromethane / 1.25 h / 0 - 20 °C
6.1: tetrahydrofuran / 0.75 h / 0 - 20 °C / Inert atmosphere
7.1: Dess-Martin periodane / dichloromethane / 1.25 h / 0 - 20 °C
8.1: hydrazine / ethanol / 1 h / 20 °C
9.1: hydrogenchloride / 1,4-dioxane / 1 h / 20 °C
10.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 0 °C / Cooling with ice
11.1: sodium hydride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere
12.1: diphosphorus pentasulfide / pyridine / 18 h / 95 °C
13.1: ammonium chloride / ethanol / 28 h / 80 °C
14.1: sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / toluene / 20 - 100 °C / Sealed tube; Inert atmosphere
15.1: hydrogenchloride / water; isopropyl alcohol / 3 h / 20 °C
16.1: HATU; ammonia / dichloromethane; N,N-dimethyl-aniline / 0.17 h / 20 °C
16.2: 18 h / 20 °C
With
hydrogenchloride; diphosphorus pentasulfide; tris-(dibenzylideneacetone)dipalladium(0); lithium aluminium tetrahydride; ammonia; sodium hydride; sodium hydrogencarbonate; ammonium chloride; Dess-Martin periodane; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; N-ethyl-N,N-diisopropylamine; HATU; sodium t-butanolate; hydrazine;
In
tetrahydrofuran; 1,4-dioxane; pyridine; methanol; ethanol; dichloromethane; water; N,N-dimethyl-aniline; isopropyl alcohol; toluene;