hydrogen; palladium on activated charcoal in ethyl acetate

1.1: NaH / dimethylformamide / 0.5 h / 20 °C 1.2: 80 percent / dimethylformamide / 0.5 h / 20 °C 2.1: 96 percent / NBS / tetrahydrofuran / 1 h / 0 °C 3.1: 100 percent / Pd2(dba)3*CHCl3; P(o-tol)3; iso-PrNEt2 / dimethylformamide / 1 h / 90 °C 4.1: 88 percent / H2 / 10 percent Pd/C / ethyl acetate View Scheme

1: 100 percent / Pd2(dba)3*CHCl3; P(o-tol)3; iso-PrNEt2 / dimethylformamide / 1 h / 90 °C 2: 88 percent / H2 / 10 percent Pd/C / ethyl acetate View Scheme

1: NaH / dimethylformamide 2: i-Pr2NEt, Pd2(dba)3, P(o-tol)3 / dimethylformamide 3: 100 percent / H2 / Pd/C / ethyl acetate View Scheme

1: 100 percent / Pd2(dba)3*CHCl3; P(o-tol)3; iso-PrNEt2 / dimethylformamide / 1 h / 90 °C 2: 88 percent / H2 / 10 percent Pd/C / ethyl acetate View Scheme

1: 96 percent / NBS / tetrahydrofuran / 1 h / 0 °C 2: 100 percent / Pd2(dba)3*CHCl3; P(o-tol)3; iso-PrNEt2 / dimethylformamide / 1 h / 90 °C 3: 88 percent / H2 / 10 percent Pd/C / ethyl acetate View Scheme

hydrogenchloride; diethyl ether; zinc(II) chloride Erwaermen des Reaktionsprodukts mit Wasser;

4-(N,N-dimethlyamino)pyridine; triethylamine; dicyclohexyl-carbodiimide in dichloromethane; toluene 1.) room temperature, 24 h, 2.) 85 deg C, 5 h 15 min;

1: potassium carbonate / dimethylsulfoxide / 2.5 h / 90 °C 2: 2.02 g / formic acid, 30percent hydrogen peroxide / 6 h / 0 - 5 °C 3: 1.) zinc cyanide, hydrogen chloride / 1.) ether, 0 deg C, 3 h, 2.) water, 15 min 4: 217 mg / pyridine / 14 h / 80 °C 5: 140 mg / potassium permanganate / acetone; H2O / 21 h 6: 22 percent / p-dimethylaminopyridine, dicyclohexylcarbodi-imide, Et3N / CH2Cl2; toluene / 1.) room temperature, 24 h, 2.) 85 deg C, 5 h 15 min View Scheme

1: 2.02 g / formic acid, 30percent hydrogen peroxide / 6 h / 0 - 5 °C 2: 1.) zinc cyanide, hydrogen chloride / 1.) ether, 0 deg C, 3 h, 2.) water, 15 min 3: 217 mg / pyridine / 14 h / 80 °C 4: 140 mg / potassium permanganate / acetone; H2O / 21 h 5: 22 percent / p-dimethylaminopyridine, dicyclohexylcarbodi-imide, Et3N / CH2Cl2; toluene / 1.) room temperature, 24 h, 2.) 85 deg C, 5 h 15 min View Scheme