lithium aluminium tetrahydride in tetrahydrofuran 2 h; Ambient temperature;

1: 1.) NaCNBH4, 2.) aq. HCl / 1.) MeOH, RT, 15 h 2: Et3N / CH2Cl2 / 0.17 h / Ambient temperature 3: 41 percent / HN03, H2SO4 / nitromethane / 1 h / -5 °C 4: NH4COOH / Pd/C / methanol / Ambient temperature 5: LiAlH4 / diethyl ether / 15 h / Ambient temperature 6: NH2OH*HCl, Na2SO4 / H2O / 1 h / Heating 7: 1.) 90 percent aq. H2SO4, 2.) LiAlH4 / 1.) a) RT, 0.5 h, b) 80 deg C, 0.5 h, 2.) diethyl ether, RT, 1 h View Scheme

1: SOCl2 / CH2Cl2 / 1.5 h / Heating 2: AlCl3 / CH2Cl2 / 2 h / -5 - 25 °C 3: 1.) NaCNBH4, 2.) aq. HCl / 1.) MeOH, RT, 15 h 4: Et3N / CH2Cl2 / 0.17 h / Ambient temperature 5: 41 percent / HN03, H2SO4 / nitromethane / 1 h / -5 °C 6: NH4COOH / Pd/C / methanol / Ambient temperature 7: LiAlH4 / diethyl ether / 15 h / Ambient temperature 8: NH2OH*HCl, Na2SO4 / H2O / 1 h / Heating 9: 1.) 90 percent aq. H2SO4, 2.) LiAlH4 / 1.) a) RT, 0.5 h, b) 80 deg C, 0.5 h, 2.) diethyl ether, RT, 1 h View Scheme

1: 41 percent / HN03, H2SO4 / nitromethane / 1 h / -5 °C 2: NH4COOH / Pd/C / methanol / Ambient temperature 3: LiAlH4 / diethyl ether / 15 h / Ambient temperature 4: NH2OH*HCl, Na2SO4 / H2O / 1 h / Heating 5: 1.) 90 percent aq. H2SO4, 2.) LiAlH4 / 1.) a) RT, 0.5 h, b) 80 deg C, 0.5 h, 2.) diethyl ether, RT, 1 h View Scheme

1: NH4COOH / Pd/C / methanol / Ambient temperature 2: LiAlH4 / diethyl ether / 15 h / Ambient temperature 3: NH2OH*HCl, Na2SO4 / H2O / 1 h / Heating 4: 1.) 90 percent aq. H2SO4, 2.) LiAlH4 / 1.) a) RT, 0.5 h, b) 80 deg C, 0.5 h, 2.) diethyl ether, RT, 1 h View Scheme

1: AlCl3 / CH2Cl2 / 2 h / -5 - 25 °C 2: 1.) NaCNBH4, 2.) aq. HCl / 1.) MeOH, RT, 15 h 3: Et3N / CH2Cl2 / 0.17 h / Ambient temperature 4: 41 percent / HN03, H2SO4 / nitromethane / 1 h / -5 °C 5: NH4COOH / Pd/C / methanol / Ambient temperature 6: LiAlH4 / diethyl ether / 15 h / Ambient temperature 7: NH2OH*HCl, Na2SO4 / H2O / 1 h / Heating 8: 1.) 90 percent aq. H2SO4, 2.) LiAlH4 / 1.) a) RT, 0.5 h, b) 80 deg C, 0.5 h, 2.) diethyl ether, RT, 1 h View Scheme

1: LiAlH4 / diethyl ether / 15 h / Ambient temperature 2: NH2OH*HCl, Na2SO4 / H2O / 1 h / Heating 3: 1.) 90 percent aq. H2SO4, 2.) LiAlH4 / 1.) a) RT, 0.5 h, b) 80 deg C, 0.5 h, 2.) diethyl ether, RT, 1 h View Scheme

1: 12.7 g / liq. NH3, 2-propanol, Na / tetrahydrofuran 2: 1.) ethereal HCl, 2.) H2NOH*HCl, pyridine, 3.) HBr, CH3COOH 3: 1.76 g / 2 N HCl / 2 h / Heating 4: 4.78 g / aq. HCl, H2NOH*HCl, Na2SO4 / 1 h / Heating 5: 2.78 percent / aq. H2SO4 / a) 0 deg C, 1 h, b) 0 deg C to 75 deg C, 0.5 h 6: 595 mg / LiAlH4 / tetrahydrofuran / 2 h / Ambient temperature View Scheme

1: p-toluenesulfonic acid monohydrate / benzene / 48 h / Heating 2: H2, PtO2 / ethanol / 2.5 h / 1520 Torr / Ambient temperature 3: 12.7 g / liq. NH3, 2-propanol, Na / tetrahydrofuran 4: 1.) ethereal HCl, 2.) H2NOH*HCl, pyridine, 3.) HBr, CH3COOH 5: 1.76 g / 2 N HCl / 2 h / Heating 6: 4.78 g / aq. HCl, H2NOH*HCl, Na2SO4 / 1 h / Heating 7: 2.78 percent / aq. H2SO4 / a) 0 deg C, 1 h, b) 0 deg C to 75 deg C, 0.5 h 8: 595 mg / LiAlH4 / tetrahydrofuran / 2 h / Ambient temperature View Scheme

1: H2, PtO2 / ethanol / 2.5 h / 1520 Torr / Ambient temperature 2: 12.7 g / liq. NH3, 2-propanol, Na / tetrahydrofuran 3: 1.) ethereal HCl, 2.) H2NOH*HCl, pyridine, 3.) HBr, CH3COOH 4: 1.76 g / 2 N HCl / 2 h / Heating 5: 4.78 g / aq. HCl, H2NOH*HCl, Na2SO4 / 1 h / Heating 6: 2.78 percent / aq. H2SO4 / a) 0 deg C, 1 h, b) 0 deg C to 75 deg C, 0.5 h 7: 595 mg / LiAlH4 / tetrahydrofuran / 2 h / Ambient temperature View Scheme