Multi-step reaction with 10 steps
1.1: tetra-(n-butyl)ammonium iodide; sodium hydride / tetrahydrofuran; mineral oil / 0 - 20 °C / Inert atmosphere
2.1: sodium azide; water; ammonium chloride / ethyl methyl ether / 5 h / Reflux
3.1: tetra-(n-butyl)ammonium iodide; sodium hydride / tetrahydrofuran; mineral oil / 20 °C / Inert atmosphere
4.1: lithium aluminium tetrahydride / tetrahydrofuran / -78 - 0 °C / Inert atmosphere
5.1: triethylamine / dichloromethane / 4 h / 20 °C / Inert atmosphere
6.1: hydrogenchloride; water / methanol / 40 °C
7.1: dmap; triethylamine / dichloromethane / 1 h / 0 °C / Inert atmosphere
8.1: di-isopropyl azodicarboxylate; triphenylphosphine / dichloromethane / 0 - 20 °C / Inert atmosphere
9.1: naphthalene; sodium / 1,2-dimethoxyethane / -60 °C / Inert atmosphere
10.1: sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 16 h / 20 °C / Inert atmosphere
10.2: 4 h / 20 °C / Inert atmosphere
With
hydrogenchloride; dmap; lithium aluminium tetrahydride; sodium azide; naphthalene; di-isopropyl azodicarboxylate; water; sodium; tetra-(n-butyl)ammonium iodide; sodium tris(acetoxy)borohydride; sodium hydride; ammonium chloride; triethylamine; triphenylphosphine;
In
tetrahydrofuran; methanol; 1,2-dimethoxyethane; ethyl methyl ether; dichloromethane; 1,2-dichloro-ethane; mineral oil;
8.1: Mitsunobu reaction;
DOI:10.1021/jo202054g