Multi-step reaction with 14 steps
1: NaN3, TBAHS / dimethylformamide
2: Ph3P, DEAD / tetrahydrofuran
3: KOH / ethanol
4: 1.) NaH, 2.) (Bu)4NI / 1.) THF, 2.) THF
5: 1N aq. H2SO4 / acetone
6: H2 / Pd/C / tetrahydrofuran
7: dioxane
8: Ph3P, DEAD / tetrahydrofuran
9: KOH / ethanol
10: HN3, PH3P, DEAD / toluene
11: H2 / Pd/C / tetrahydrofuran
12: N-<3-(dimethylamino)propyl>-N'-ethyl-carbodiimide, DMAP / CH2Cl2
13: H2 / Pd/C / methanol
14: p-TsOH, DMAP / CH2Cl2
With
dmap; potassium hydroxide; sodium azide; tris-(2-chloro-ethyl)-amine; sulfuric acid; hydrogen; tetra(n-butyl)ammonium hydrogensulfate; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triphenylphosphine; diethylazodicarboxylate;
palladium on activated charcoal;
In
tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; acetone; toluene;