Multi-step reaction with 10 steps
1.1: sodium hexamethyldisilazane / tetrahydrofuran / 1.17 h / -78 °C / Inert atmosphere
1.2: 1 h / -78 °C
2.1: lithium aluminium tetrahydride / tetrahydrofuran / 48.17 h / -78 °C / Inert atmosphere
3.1: lithium borohydride / tetrahydrofuran / 72.5 h / 20 - 50 °C
4.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 20 °C
5.1: sodium azide / dimethyl sulfoxide / 96 h / 120 °C
6.1: sodium tetrahydroborate; nickel (II) chloride hexahydrate / methanol / 1 h / 0 °C
7.1: potassium carbonate / acetonitrile / 15 h / 20 °C
8.1: formic acid; iron / methanol / 19 h / 65 °C
9.1: hydrogen bromide / 1,4-dioxane; water / 32 h / 80 °C
9.2: 20 °C / pH 11
10.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 20 °C
With
sodium tetrahydroborate; lithium aluminium tetrahydride; lithium borohydride; formic acid; sodium azide; nickel (II) chloride hexahydrate; hydrogen bromide; sodium hexamethyldisilazane; iron; potassium carbonate; N-ethyl-N,N-diisopropylamine;
In
tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; dimethyl sulfoxide; acetonitrile;