Multi-step reaction with 7 steps
1: 80 percent / 65percent HClO4 / 10percent Pd/charcoal / dioxane; ethanol / 20 h / 55 - 60 °C
2: 90 percent / 1) tert-BuOK / dimethylformamide / 1) 10 min, 2) 1 h
3: 90 percent / H2 / 10percent Pd/charcoal / CH2Cl2; methanol / 836 Torr / 1) water bath, 2) 15-20 deg C, 9 h
4: 100 percent / BBr3 / CH2Cl2 / 1) -78 deg C, 10 min, 2) r.t., 1 h
5: 235 mg / (dimethylamino)pyridine, dicycylohexylcarbodiimide / dimethylformamide / 0 deg C, 5 min -> 20 deg C, 3 h
6: 70 percent / 1) 1 N lithium triethylborohydride, 2) 1 N HCl / tetrahydrofuran / 2.5 h / 0 °C
7: 1) tert-BuOK / dimethylformamide / 1) 0 deg C, 10 min, 2) 0->20 deg C, 1.5 h
With
hydrogenchloride; dmap; perchloric acid; potassium tert-butylate; hydrogen; boron tribromide; lithium triethylborohydride; dicyclohexyl-carbodiimide;
palladium on activated charcoal;
In
tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja00332a042