pyridinium chlorochromate in dichloromethane 2 h;

1: 95 percent / borane dimethyl sulfide complex / tetrahydrofuran / 0 - 20 °C 2: 52 percent / MnO2 / CHCl3 / 20 °C View Scheme

1: 70 percent / potassium permanganate, pyridine / H2O / 1.) 50 deg C, 3 h, 2.) RT, 3 h 2: 95 percent / LiAlH4 / diethyl ether / 3 h / Ambient temperature 3: 95 percent / pyridinium chlorochromate / CH2Cl2 / 2 h View Scheme

1: 84 percent / K2CO3 / acetone / 5 h / Heating 2: 70 percent / potassium permanganate, pyridine / H2O / 1.) 50 deg C, 3 h, 2.) RT, 3 h 3: 95 percent / LiAlH4 / diethyl ether / 3 h / Ambient temperature 4: 95 percent / pyridinium chlorochromate / CH2Cl2 / 2 h View Scheme

1: 1.) 6 M sulfuric acid, NaNO2, 2.) CuSO4*5H2O, 96percent H2SO4 / 1.) water, 2.) 165 deg C 2: 84 percent / K2CO3 / acetone / 5 h / Heating 3: 70 percent / potassium permanganate, pyridine / H2O / 1.) 50 deg C, 3 h, 2.) RT, 3 h 4: 95 percent / LiAlH4 / diethyl ether / 3 h / Ambient temperature 5: 95 percent / pyridinium chlorochromate / CH2Cl2 / 2 h View Scheme

1: malonic acid / pyridine 2: diphenyl phosphoryl azide; triethylamine / ethyl acetate; benzene 3: diphenylether 4: methanol 5: ethyl acetate; trichlorophosphate View Scheme

1.1: piperidine; pyridine / 13 h / Reflux 2.1: hydrogen / palladium 10 on activated carbon / ethanol / 20 °C 3.1: methanesulfonic acid / 0.17 h / 90 °C / Microwave irradiation; Sealed 3.2: pH 7 / Cooling with ice View Scheme

caesium carbonate in N,N-dimethyl-formamide T=100°C; 1 h; Inert atmosphere;

potassium carbonate in N,N-dimethyl-formamide T=100°C; Product distribution / selectivity;

1: With piperidine; pyridine T=80°C; 4 - 18 h; Heating / reflux; 2: With hydrogenchloride in water Product distribution / selectivity;