2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; tetrabutylammomium bromide in dichloromethane; water 1 h;

1.1: 85 percent / TsOH / benzene / 16 h / Heating 2.1: Na / tetrahydrofuran; propan-2-ol 2.2: 20 percent / 4N HCl / diethyl ether; dioxane / 2 h / 0 °C 3.1: 0.6 percent / HCO2NH4 / Pd/C / methanol / Heating 4.1: 1.1 g / NaHCO3 / acetone / 24 h 5.1: 70 percent / TEMPO; nBu4NBr; NaOCl / CH2Cl2; H2O / 1 h View Scheme

1.1: Na / tetrahydrofuran; propan-2-ol 1.2: 20 percent / 4N HCl / diethyl ether; dioxane / 2 h / 0 °C 2.1: 0.6 percent / HCO2NH4 / Pd/C / methanol / Heating 3.1: 1.1 g / NaHCO3 / acetone / 24 h 4.1: 70 percent / TEMPO; nBu4NBr; NaOCl / CH2Cl2; H2O / 1 h View Scheme

1: H2 / Pd/C / aq. ethanol / 48 h / 2585.81 Torr 2: 6.31 g / NaHCO3 / acetone; H2O / 0 - 20 °C View Scheme

sodium hydrogencarbonate in water; acetone T=0 - 20°C;

1: 1.1 g / NaHCO3 / acetone / 24 h 2: 70 percent / TEMPO; nBu4NBr; NaOCl / CH2Cl2; H2O / 1 h View Scheme