Multi-step reaction with 14 steps
1.1: copper(I) bromide dimethylsulfide complex / tetrahydrofuran / 0.25 h / -78 °C
1.2: 5 h / -78 °C
2.1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol / 1 h / -15 - 20 °C
3.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 72 h / 0 - 20 °C
4.1: ozone / dichloromethane / -78 °C
4.2: 1 h / -78 - 20 °C / Inert atmosphere
4.3: 1 h / 0 °C / Inert atmosphere
5.1: trifluoroacetic acid / dichloromethane / 2 h / 0 - 20 °C
6.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 0 - 20 °C
7.1: hydrazine hydrate / ethanol / 2 h / Reflux
8.1: sodium cyanoborohydride; acetic acid / methanol / 0 °C
9.1: methanol / 72 h / Reflux
10.1: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / -15 - 20 °C
10.2: 2 h / 0 °C
11.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran
12.1: hydrazine / ethanol / 80 °C
13.1: triethylamine / dichloromethane / 1 h / 0 - 20 °C
14.1: hydrogenchloride / methanol; 1,4-dioxane / 12 h
With
hydrogenchloride; sodium tetrahydroborate; lithium aluminium tetrahydride; copper(I) bromide dimethylsulfide complex; cerium(III) chloride heptahydrate; di-isopropyl azodicarboxylate; sodium cyanoborohydride; ozone; hydrazine hydrate; acetic acid; triethylamine; triphenylphosphine; trifluoroacetic acid; hydrazine;
In
tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane;
DOI:10.1039/c3md00021d