quinoline; hydrogen; Lindlar's catalyst in pentane T=0°C; 4 h;

1.1: lithium diisopropylamide / tetrahydrofuran / 0.25 h / -78 °C 1.2: 97 percent / tetrahydrofuran / 18 h / 20 - 25 °C 2.1: 89 percent / hydrogen peroxide; aq. sodium hydroxide / diethyl ether / 2 h / 25 °C 3.1: 69 percent / p-toluenesulfonic acid / CH2Cl2 / 2 h / 100 °C 4.1: 65 percent / hydrogen / palladium on calcium carbonate / pentane / 1 h / 0 °C / 760 Torr View Scheme

1: NaOH / methanol / 0.25 h / Heating 2: 0.5 h / 120 °C / 0.2 Torr 3: 71.7 percent / H2, quinoline / 5percent Pd/CaCO3 / pentane / 1 h / 0 °C View Scheme

1.1: ozone / CH2Cl2 / 0.42 h / -78 °C 1.2: PPh3 / CH2Cl2 / 2 h / -78 °C 1.3: 86 percent / N-iodosuccinimide; N-tetrabutylammonium iodide / CH2Cl2 / 0.25 h / 20 °C 2.1: 94 percent / H2; quinoine / Lindlar catalyst / pentane / 4 h / 0 °C View Scheme

1.1: MeSO3H / methanol / 8 h / Heating 1.2: 89 percent / Ba(OH)2*8H2O / methanol / 2 h / Heating 2.1: ozone / CH2Cl2 / 0.42 h / -78 °C 2.2: PPh3 / CH2Cl2 / 2 h / -78 °C 2.3: 86 percent / N-iodosuccinimide; N-tetrabutylammonium iodide / CH2Cl2 / 0.25 h / 20 °C 3.1: 94 percent / H2; quinoine / Lindlar catalyst / pentane / 4 h / 0 °C View Scheme

1: Chirald, LiAlH4 / diethyl ether / 1.) -100 deg C, 2 h, 2.) -70 to -65 deg C, 2 h 2: 71.7 percent / H2, quinoline / 5percent Pd/CaCO3 / pentane / 1 h / 0 °C View Scheme

1: 30 percent / NaBH4 / CH2Cl2; methanol / 0.25 h / 0 °C 2: 99 percent / imidazole, DMAP / dimethylformamide / 0.75 h / 0 °C 3: 85 percent / NCS, AgNO3 / acetonitrile; H2O; CH2Cl2 / 0.12 h / 0 °C 4: 1.) Ph3P / 1.) CH2Cl2, 0 deg C, 1h, 2.) -78 deg C, 40 min 5: 1.) BuLi / 1.) THF, hexane, -78 deg C, 1h, 2.) THF, hexane, HMPA, RT, 30 min 6: 99 percent / H2 / Lindlar catalyst / ethyl acetate / 0.5 h / Ambient temperature 7: 70 percent / Bu4NF / tetrahydrofuran / 1 h / Ambient temperature 8: 1.) DMSO/oxalyl chloride, 2.) NEt3 / 1.) CH2Cl2, -78 deg C, 30 min, 2.) -78 deg C to 0 deg C 9: 70percent ButOOH, 10percent aq. NaOH / tetrahydrofuran / 0.5 h / 0 °C 10: 1.) KOH, 2.) Ph3P, diethyl azodicarboxylate / 1.) MeOH, 60 deg C, 3h, 2.) benzene, RT, 13h View Scheme

1: 80 percent / diisopropyl ether / 10 h / Ambient temperature; lipase PS 2: 81 percent / 5percent KOH, methanol / 0.25 h / Heating 3: 91 percent / H2, quinoline / Lindlar catalyst / pentane / 5 h / 0 °C View Scheme

1: 1.) Ph3P / 1.) CH2Cl2, 0 deg C, 1h, 2.) -78 deg C, 40 min 2: 1.) BuLi / 1.) THF, hexane, -78 deg C, 1h, 2.) THF, hexane, HMPA, RT, 30 min 3: 99 percent / H2 / Lindlar catalyst / ethyl acetate / 0.5 h / Ambient temperature 4: 70 percent / Bu4NF / tetrahydrofuran / 1 h / Ambient temperature 5: 1.) DMSO/oxalyl chloride, 2.) NEt3 / 1.) CH2Cl2, -78 deg C, 30 min, 2.) -78 deg C to 0 deg C 6: 70percent ButOOH, 10percent aq. NaOH / tetrahydrofuran / 0.5 h / 0 °C 7: 1.) KOH, 2.) Ph3P, diethyl azodicarboxylate / 1.) MeOH, 60 deg C, 3h, 2.) benzene, RT, 13h View Scheme

1: 1.) Ph3P / 1.) CH2Cl2, 0 deg C, 1h, 2.) -78 deg C, 40 min 2: 1.) BuLi / 1.) THF, hexane, -78 deg C, 1h, 2.) THF, hexane, HMPA, RT, 30 min 3: 95 percent / H2 / Lindlar catalyst / ethyl acetate / 0.5 h / Ambient temperature 4: 68 percent / Bu4NF / tetrahydrofuran / 1 h / Ambient temperature 5: 1.) DMSO/oxalyl chloride, 2.) NEt3 / 1.) CH2Cl2, -78 deg C, 30 min, 2.) -78 deg C to 0 deg C 6: 70percent ButOOH, 10percent aq. NaOH / tetrahydrofuran / 0.5 h / 0 °C 7: 1.) KOH, 2.) Ph3P, diethyl azodicarboxylate / 1.) MeOH, 60 deg C, 3h, 2.) benzene, RT, 13h View Scheme