Multi-step reaction with 13 steps
1.1: 87 percent / p-toluenesulfonic acid / 24 h / 22 °C
2.1: 100 percent / pyridine / 5 h
3.1: 92 percent / NaH / dimethylformamide / 1 h
4.1: 80 percent / LiAlH4 / tetrahydrofuran / 2 h
5.1: 97 percent / Et3N / CH2Cl2 / 0.5 h
6.1: NaH; KI / dimethylformamide; tetrahydrofuran / 12 h / 65 °C
7.1: 0.069 g / Bu4NF / tetrahydrofuran / 22 °C
8.1: 93 percent / aq. HCl / tetrahydrofuran / 12 h / 22 °C
9.1: 89 percent / p-toluenesulfonic acid / acetonitrile / 22 °C
10.1: 99 percent / 4-dimethylaminopyridine / CH2Cl2; pyridine / 22 °C
11.1: 2,6-di-tert-butyl-4-methylpyridine / dioxane / 22 °C
11.2: 64 percent / dimethyl(methylthio)sulfonium triflate / dioxane
12.1: H2S / H2O; pyridine
12.2: 92 percent / aq. NaOAc / tetrahydrofuran / 22 °C
13.1: 83 percent / aq. CF3COOH / CH2Cl2 / 0 °C
With
hydrogenchloride; dmap; lithium aluminium tetrahydride; 2,6-di-tert-butyl-4-methylpyridine; hydrogen sulfide; tetrabutyl ammonium fluoride; sodium hydride; toluene-4-sulfonic acid; triethylamine; trifluoroacetic acid; potassium iodide;
In
tetrahydrofuran; 1,4-dioxane; pyridine; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/S0968-0896(01)00015-3