1: tetrabutylammonium iodide, sodium hydride / tetrahydrofuran / 0.75 h / Heating 2: hydrochloric acid / methanol; H2O / 20 h / Ambient temperature 3: sodium methoxide / 3 h / Heating 4: acid resin (Dowex 50W-XH) / methanol / 12 h / Heating 5: pyridine / CH2Cl2; pyridine / 0.25 h / -30 °C 6: sodium azide / dimethylformamide / 24 h / 50 °C 7: 80 percent / sodium metoxide / methanol / 6 h / Ambient temperature 8: 81 percent / pyridine / 4 h / from 0 deg C to room temp. 9: 94 percent / pyridine / 4 h / Ambient temperature 10: 82 percent / sodium methoxide / dimethylformamide / 0.08 h / 50 °C 11: sodium methoxide / dimethylformamide / 3 h / 50 °C 12: hydrogen / palladium black / ethanol / 1 h 13: aq. sodium bicarbonate / diethyl ether / 2 h / Ambient temperature 14: 1.) 50percent aq. trifluoroacetic acid, 2.) sodium borohydride / 1.) room temp., 15 ethanol, min; 2.) water, room temp., 10 min 15: 70 percent / hydrogen / palladium black / acetic acid / 13 h View Scheme

1: 86 percent / n-C4H9Li / toluene / 48 h / 40 °C 2: 1.) DCC, 2.) pyridinium trifluoroacetate, 3.) NH2OH*HCl, KHCO3 3: 1.) LAH, 2.) K2CO3 / 1.) ether 4: 2.) KCl, 3.) I2, HOAc 5: 100 percent / 50percent KOH / ethanol / 18 h / Heating 6: 99 percent / H2 / Pd/C / ethanol View Scheme

1: 1.) DCC, 2.) pyridinium trifluoroacetate, 3.) NH2OH*HCl, KHCO3 2: 1.) LAH, 2.) K2CO3 / 1.) ether 3: 2.) KCl, 3.) I2, HOAc 4: 100 percent / 50percent KOH / ethanol / 18 h / Heating 5: 99 percent / H2 / Pd/C / ethanol View Scheme

1: 1.) LAH, 2.) K2CO3 / 1.) ether 2: 2.) KCl, 3.) I2, HOAc 3: 100 percent / 50percent KOH / ethanol / 18 h / Heating 4: 99 percent / H2 / Pd/C / ethanol View Scheme

hydrogenchloride; hydrogen; palladium on activated charcoal in methanol 2.5 h;

1: With hydrogenchloride; palladium 10 on activated carbon; hydrogen in ethanol; water T=20°C; 16 h; 2: in ethanol; water 3: With ammonium hydroxide in water

Dowex 50W-X8; sodium acetate; palladium on activated charcoal 1.) 95percent methanol, reflux, 2.) methanol; Yield given. Multistep reaction;

1.1: 100 percent / methanol / 0.25 h 2.1: LiBH4 / tetrahydrofuran / 8 h / 20 °C 2.2: DMAP; Ac2O / pyridine; CH2Cl2 / 2 h 2.3: aq. HCl / 18 h / Heating View Scheme

1.1: sulfuric acid; copper(II) sulfate / 28 h / 25 °C 1.2: 3.5 h / 25 °C 2.1: sodium hydride; tetra-(n-butyl)ammonium iodide / tetrahydrofuran / 0 °C / |Reflux 3.1: sulfuric acid / 1,4-dioxane / 4 h / |Reflux 4.1: 2,2,2-trifluoroethanol / 24 h / 25 °C 5.1: triethylamine / dichloromethane / 4 h / -10 - 40 °C 5.2: 0 °C 6.1: hydrogen; acetic acid; palladium hydroxide on carbon; palladium / 18 h / 20 °C / 760.05 Torr View Scheme

1.1: sodium hydride; tetra-(n-butyl)ammonium iodide / tetrahydrofuran / 0 °C / |Reflux 2.1: sulfuric acid / 1,4-dioxane / 4 h / |Reflux 3.1: 2,2,2-trifluoroethanol / 24 h / 25 °C 4.1: triethylamine / dichloromethane / 4 h / -10 - 40 °C 4.2: 0 °C 5.1: hydrogen; acetic acid; palladium hydroxide on carbon; palladium / 18 h / 20 °C / 760.05 Torr View Scheme