1: NaBH4 / 1,2-dimethoxy-ethane / 48 h / 90 - 95 °C 2: 87 percent / AG 1-X4(OH-) / methanol / 2 h / Ambient temperature 3: 81 percent / NaN3, NH4Cl / 2-methoxy-ethanol; H2O / 2 h / 100 °C 4: 330 mg / pyridine / 6 h / 0 °C 5: 170 mg / dimethylformamide / 28 h / 135 °C View Scheme

sodium tetrahydroborate in ethylene glycol dimethyl ether T=90 - 95°C; 48 h; Yield given;

1: NaBH4 / 1,2-dimethoxy-ethane / 48 h / 90 - 95 °C 2: 87 percent / AG 1-X4(OH-) / methanol / 2 h / Ambient temperature 3: 81 percent / NaN3, NH4Cl / 2-methoxy-ethanol; H2O / 2 h / 100 °C 4: H2 / 10percent Pd/C / methanol / 15 h / 2280 Torr View Scheme

1: NaBH4 / 1,2-dimethoxy-ethane / 48 h / 90 - 95 °C 2: 87 percent / AG 1-X4(OH-) / methanol / 2 h / Ambient temperature 3: 81 percent / NaN3, NH4Cl / 2-methoxy-ethanol; H2O / 2 h / 100 °C 4: 330 mg / pyridine / 6 h / 0 °C 5: 170 mg / dimethylformamide / 28 h / 135 °C 6: 46 percent / 0.1 N NaOH / methanol; H2O / 6.5 h / Ambient temperature View Scheme

1: NaBH4 / 1,2-dimethoxy-ethane / 48 h / 90 - 95 °C 2: 87 percent / AG 1-X4(OH-) / methanol / 2 h / Ambient temperature 3: 81 percent / NaN3, NH4Cl / 2-methoxy-ethanol; H2O / 2 h / 100 °C 4: 330 mg / pyridine / 6 h / 0 °C View Scheme

1: NaBH4 / 1,2-dimethoxy-ethane / 48 h / 90 - 95 °C 2: 87 percent / AG 1-X4(OH-) / methanol / 2 h / Ambient temperature 3: 81 percent / NaN3, NH4Cl / 2-methoxy-ethanol; H2O / 2 h / 100 °C View Scheme