1: With caesium carbonate; copper(I) bromide in xylenes T=130°C; 16 h; 2: With hydrogenchloride in tert-butyl methyl ether; isopropyl alcohol; xylenes T=20°C;

hydrogenchloride; potassium hydroxide in sulfolane; water; toluene

1: (3-hydroxy-3-phenyl-propyl)-carbamic acid benzyl ester With sodium hydride in dimethyl sulfoxide T=60°C; 1 h; 2: 1-chloro-4-(trifluoromethyl)benzene in dimethyl sulfoxide T=100°C; 1 h; 3: With hydrogenchloride in diethyl ether T=20°C;

hydrogenchloride in diethyl ether 0.5 h;

in isobutyramide; water; toluene

1.1: 54 percent / cerium ammonium nitrate / acetonitrile / 0.5 h / Heating 2.1: 100 percent / aq. lithium hydroxide / tetrahydrofuran / 1 h / Heating 3.1: lithium aluminum hydride / tetrahydrofuran 4.1: sodium hydride / dimethylsulfoxide / 1 h / 60 °C 4.2: dimethylsulfoxide / 1 h / 100 °C 4.3: 52 percent / aq. hydrochloric acid / diethyl ether / 20 °C View Scheme

1.1: OsO4; NMO 2.1: 54 percent / cerium ammonium nitrate / acetonitrile / 0.5 h / Heating 3.1: 100 percent / aq. lithium hydroxide / tetrahydrofuran / 1 h / Heating 4.1: lithium aluminum hydride / tetrahydrofuran 5.1: sodium hydride / dimethylsulfoxide / 1 h / 60 °C 5.2: dimethylsulfoxide / 1 h / 100 °C 5.3: 52 percent / aq. hydrochloric acid / diethyl ether / 20 °C View Scheme

1.1: 100 percent / aq. lithium hydroxide / tetrahydrofuran / 1 h / Heating 2.1: lithium aluminum hydride / tetrahydrofuran 3.1: sodium hydride / dimethylsulfoxide / 1 h / 60 °C 3.2: dimethylsulfoxide / 1 h / 100 °C 3.3: 52 percent / aq. hydrochloric acid / diethyl ether / 20 °C View Scheme

1.1: lithium aluminum hydride / tetrahydrofuran 2.1: sodium hydride / dimethylsulfoxide / 1 h / 60 °C 2.2: dimethylsulfoxide / 1 h / 100 °C 2.3: 52 percent / aq. hydrochloric acid / diethyl ether / 20 °C View Scheme

1.1: triethylamine / dichloromethane / 1 h / 0 °C / Inert atmosphere 2.1: triethylamine / dichloromethane / 8 h / 25 °C / Inert atmosphere 3.1: triphenylphosphine / dichloromethane / 0.25 h / 0 °C / Inert atmosphere 3.2: 0 - 25 °C / Inert atmosphere 4.1: silver nitrate / acetonitrile / 6 h / Reflux; Inert atmosphere; Darkness 5.1: water / pH 7 - 8 / aq. phosphate buffer View Scheme