Wilkinson's catalyst in benzene T=120°C; 24 h;

sodium hydroxide; hydrazine hydrate in 1,2-bis-(2-hydroxyethoxy)-ethane 7 h; Heating;

1: With hydrazine monohydrochloride; hydrazine in diethylene glycol T=125°C; Huang-Minlon reduction; 2: With potassium hydroxide in diethylene glycol T=210°C;

1.1: 79 percent / Li / tetrahydrofuran / 0.75 h 2.1: 89 percent / PCC; silica gel / CH2Cl2 / 2 h 3.1: 80 percent / tetrahydrofuran / 4 h 4.1: 76 percent / PCC; silica gel / CH2Cl2 / 24 h 5.1: 81 percent / NaBH4 / methanol / 0 - 5 °C 6.1: 45 percent / EtCOOH / 48 h / 180 °C 7.1: 94 percent / PhCH=RuCl2(PCy3)2 / CH2Cl2 / 10 h / 20 °C 8.1: 99 percent / H2 / Pd/C / ethanol / 6 h 9.1: LAH / diethyl ether / 1 h / 0 - 5 °C 9.2: PCC; silica gel / CH2Cl2 / 0.5 h 10.1: 66 percent / (Ph3P)3RhCl / benzene / 24 h / 120 °C View Scheme

1.1: 79 percent / Li / tetrahydrofuran / 0.75 h 2.1: 89 percent / PCC; silica gel / CH2Cl2 / 2 h 3.1: 80 percent / tetrahydrofuran / 4 h 4.1: 76 percent / PCC; silica gel / CH2Cl2 / 24 h 5.1: 81 percent / NaBH4 / methanol / 0 - 5 °C 6.1: 45 percent / EtCOOH / 48 h / 180 °C 7.1: 94 percent / PhCH=RuCl2(PCy3)2 / CH2Cl2 / 10 h / 20 °C 8.1: 99 percent / H2 / Pd/C / ethanol / 6 h 9.1: LAH / diethyl ether / 1 h / 0 - 5 °C 9.2: PCC; silica gel / CH2Cl2 / 0.5 h 10.1: 66 percent / (Ph3P)3RhCl / benzene / 24 h / 120 °C View Scheme

1.1: 80 percent / tetrahydrofuran / 4 h 2.1: 76 percent / PCC; silica gel / CH2Cl2 / 24 h 3.1: 81 percent / NaBH4 / methanol / 0 - 5 °C 4.1: 45 percent / EtCOOH / 48 h / 180 °C 5.1: 94 percent / PhCH=RuCl2(PCy3)2 / CH2Cl2 / 10 h / 20 °C 6.1: 99 percent / H2 / Pd/C / ethanol / 6 h 7.1: LAH / diethyl ether / 1 h / 0 - 5 °C 7.2: PCC; silica gel / CH2Cl2 / 0.5 h 8.1: 66 percent / (Ph3P)3RhCl / benzene / 24 h / 120 °C View Scheme

1.1: 89 percent / PCC; silica gel / CH2Cl2 / 2 h 2.1: 80 percent / tetrahydrofuran / 4 h 3.1: 76 percent / PCC; silica gel / CH2Cl2 / 24 h 4.1: 81 percent / NaBH4 / methanol / 0 - 5 °C 5.1: 45 percent / EtCOOH / 48 h / 180 °C 6.1: 94 percent / PhCH=RuCl2(PCy3)2 / CH2Cl2 / 10 h / 20 °C 7.1: 99 percent / H2 / Pd/C / ethanol / 6 h 8.1: LAH / diethyl ether / 1 h / 0 - 5 °C 8.2: PCC; silica gel / CH2Cl2 / 0.5 h 9.1: 66 percent / (Ph3P)3RhCl / benzene / 24 h / 120 °C View Scheme

1.1: 76 percent / PCC; silica gel / CH2Cl2 / 24 h 2.1: 81 percent / NaBH4 / methanol / 0 - 5 °C 3.1: 45 percent / EtCOOH / 48 h / 180 °C 4.1: 94 percent / PhCH=RuCl2(PCy3)2 / CH2Cl2 / 10 h / 20 °C 5.1: 99 percent / H2 / Pd/C / ethanol / 6 h 6.1: LAH / diethyl ether / 1 h / 0 - 5 °C 6.2: PCC; silica gel / CH2Cl2 / 0.5 h 7.1: 66 percent / (Ph3P)3RhCl / benzene / 24 h / 120 °C View Scheme

1.1: 99 percent / H2 / Pd/C / ethanol / 6 h 2.1: LAH / diethyl ether / 1 h / 0 - 5 °C 2.2: PCC; silica gel / CH2Cl2 / 0.5 h 3.1: 66 percent / (Ph3P)3RhCl / benzene / 24 h / 120 °C View Scheme

1.1: LAH / diethyl ether / 1 h / 0 - 5 °C 1.2: PCC; silica gel / CH2Cl2 / 0.5 h 2.1: 66 percent / (Ph3P)3RhCl / benzene / 24 h / 120 °C View Scheme