1: With oxalyl dichloride; dimethyl sulfoxide in dichloromethane T=-70°C; 0.25 h; 2: With triethylamine T=-70°C; 0.0833333 h; 3: in dichloromethane T=20°C;

hydrogenchloride in water; acetone Inert atmosphere;

1.1: NaH / dimethylformamide / 1.5 h / 20 °C 1.2: 92 percent / dimethylformamide / 1 h / 75 °C 2.1: 97 percent / H2 / Pd/C / ethanol / 20 h / 20 °C / 3750.3 Torr 3.1: 92 percent / oxalylchloride; DMSO; Et3N / CH2Cl2 / 4 h / -78 - 20 °C View Scheme

1: 97 percent / H2 / Pd/C / ethanol / 20 h / 20 °C / 3750.3 Torr 2: 92 percent / oxalylchloride; DMSO; Et3N / CH2Cl2 / 4 h / -78 - 20 °C View Scheme

formic acid T=45°C; 3 h; Inert atmosphere;

1: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 16 h / Inert atmosphere 2: sodium hypochlorite; 2,2,6,6-tetramethyl-1-piperidinyloxy, free radical; sodium hydrogencarbonate; potassium bromide / dichloromethane; water / 2.5 h / 5 °C / Inert atmosphere 3: toluene-4-sulfonic acid / tert-butyl methyl ether / 3 h / Inert atmosphere; Reflux 4: sodium hydride / N,N-dimethyl-formamide / 4 h / 40 °C / Inert atmosphere 5: hydrogenchloride / water; acetone / Inert atmosphere View Scheme

1: sodium hypochlorite; 2,2,6,6-tetramethyl-1-piperidinyloxy, free radical; sodium hydrogencarbonate; potassium bromide / dichloromethane; water / 2.5 h / 5 °C / Inert atmosphere 2: toluene-4-sulfonic acid / tert-butyl methyl ether / 3 h / Inert atmosphere; Reflux 3: sodium hydride / N,N-dimethyl-formamide / 4 h / 40 °C / Inert atmosphere 4: hydrogenchloride / water; acetone / Inert atmosphere View Scheme

1: toluene-4-sulfonic acid / tert-butyl methyl ether / 3 h / Inert atmosphere; Reflux 2: sodium hydride / N,N-dimethyl-formamide / 4 h / 40 °C / Inert atmosphere 3: hydrogenchloride / water; acetone / Inert atmosphere View Scheme

1: sodium hydride / N,N-dimethyl-formamide / 4 h / 40 °C / Inert atmosphere 2: hydrogenchloride / water; acetone / Inert atmosphere View Scheme

1.1: hydrogenchloride / water / 2 h / 50 °C / Inert atmosphere 1.2: 2 h / 0 - 20 °C / Inert atmosphere 2.1: sodium hydride / tetrahydrofuran / 16 h / Inert atmosphere; Reflux 3.1: formic acid / 3 h / 45 °C / Inert atmosphere View Scheme