Multi-step reaction with 10 steps
1.1: titanium(IV) oxide / tetrahydrofuran / Reflux
2.1: zinc / diethyl ether / 5 h / Inert atmosphere; Reflux
3.1: lithium borohydride / tetrahydrofuran / 0 - 20 °C
4.1: hydrogenchloride / 1,4-dioxane / 23 °C
5.1: ethanol / 23 °C / Inert atmosphere; Sealed tube
6.1: hydrogen / palladium-on-charcoal / ethanol / 1 h / 23 °C
7.1: 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride / methanol / 0.5 h / 0 °C
7.2: 0 °C
8.1: dichloromethane / 0 - 20 °C
9.1: potassium tert-butylate / N,N-dimethyl-formamide / 2 h / 20 °C
10.1: trifluoroacetic acid / dichloromethane / 6.5 h / 0 - 20 °C
With
hydrogenchloride; lithium borohydride; potassium tert-butylate; hydrogen; titanium(IV) oxide; trifluoroacetic acid; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride; zinc;
palladium-on-charcoal;
In
tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide;
2.1: Reformatsky Reaction;