1: 330 mg / pyridine / 6 h / 0 °C 2: 170 mg / dimethylformamide / 28 h / 135 °C View Scheme

hydrogen; triethylamine; palladium on activated charcoal in ethanol P=760 Torr; 6 h;

sodium azide; ammonium chloride in ethanol 24 h; Heating;

1: 78 percent / H2 / 10percent Pd/C / ethyl acetate / Ambient temperature 2: 1) Ba(OH)2*8H2O, 2) H2SO4 / 1) water, room temp., 2) <10 degC -> room temp., overnight 3: AG 50-X4(H+) / 120 h / Ambient temperature 5: 51 percent / pyridine / refrigerator, overnight 6: 87 percent / AG 1-X4(OH-) / methanol / 2 h / Ambient temperature 7: 81 percent / NaN3, NH4Cl / 2-methoxy-ethanol; H2O / 2 h / 100 °C View Scheme

1: 1) Ba(OH)2*8H2O, 2) H2SO4 / 1) water, room temp., 2) <10 degC -> room temp., overnight 2: AG 50-X4(H+) / 120 h / Ambient temperature 4: 51 percent / pyridine / refrigerator, overnight 5: 87 percent / AG 1-X4(OH-) / methanol / 2 h / Ambient temperature 6: 81 percent / NaN3, NH4Cl / 2-methoxy-ethanol; H2O / 2 h / 100 °C View Scheme

1: AG 50-X4(H+) / 120 h / Ambient temperature 3: 51 percent / pyridine / refrigerator, overnight 4: 87 percent / AG 1-X4(OH-) / methanol / 2 h / Ambient temperature 5: 81 percent / NaN3, NH4Cl / 2-methoxy-ethanol; H2O / 2 h / 100 °C View Scheme

1: 98 percent / NaHCO3 / toluene / 2.5 h / 86 °C 2: 78 percent / H2 / 10percent Pd/C / ethyl acetate / Ambient temperature 3: 1) Ba(OH)2*8H2O, 2) H2SO4 / 1) water, room temp., 2) <10 degC -> room temp., overnight 4: AG 50-X4(H+) / 120 h / Ambient temperature 6: 51 percent / pyridine / refrigerator, overnight 7: 87 percent / AG 1-X4(OH-) / methanol / 2 h / Ambient temperature 8: 81 percent / NaN3, NH4Cl / 2-methoxy-ethanol; H2O / 2 h / 100 °C View Scheme

1: H2O / 80 °C 2: glacial acetic acid; sodium azide / H2O / 20 °C 3: pyridine; 4-dimethylaminopyridine / 20 °C 4: 1.80 g / montmorillonite K-10 / benzene / Heating 5: potassium carbonate / methanol / 16 h / 20 °C View Scheme

1: 42 percent / Na/NH3 / tetrahydrofuran 2: NIS, P(C6H5)3 / dimethylformamide / 1 h / 50 °C 3: H2 / Ra-Ni / methanol / Heating 4: 51 percent / pyridine / refrigerator, overnight 5: 87 percent / AG 1-X4(OH-) / methanol / 2 h / Ambient temperature 6: 81 percent / NaN3, NH4Cl / 2-methoxy-ethanol; H2O / 2 h / 100 °C View Scheme

1: AG 50-X4(H+) / methanol / Ambient temperature 2: NIS, P(C6H5)3 / dimethylformamide / 1 h / 50 °C 3: H2 / Ra-Ni / methanol / Heating 4: 51 percent / pyridine / refrigerator, overnight 5: 87 percent / AG 1-X4(OH-) / methanol / 2 h / Ambient temperature 6: 81 percent / NaN3, NH4Cl / 2-methoxy-ethanol; H2O / 2 h / 100 °C View Scheme