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 7: 330 mg / pyridine / 6 h / 0 °C 8: 170 mg / dimethylformamide / 28 h / 135 °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 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 7: H2 / 10percent Pd/C / methanol / 15 h / 2280 Torr 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 7: 330 mg / pyridine / 6 h / 0 °C 8: 170 mg / dimethylformamide / 28 h / 135 °C 9: 46 percent / 0.1 N NaOH / methanol; H2O / 6.5 h / Ambient temperature 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 7: 330 mg / pyridine / 6 h / 0 °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