sodium bis(2-methoxyethoxy)aluminium dihydride in toluene 4 h; Ambient temperature; Yield given;

1: 56 percent / 1,1-(azodicarbonyl)dipiperidine; PBu3 / tetrahydrofuran / 40 °C 2: Et3N / CH2Cl2 / 40 °C 3: MeOH / Heating View Scheme

1: 1.) NaOH / 1.) H2O, 70 deg C; 2.) H2O, 70 deg C, 2.5 h 2: 61 percent / pyridine / 2 h / -10 °C 3: 84 percent / Et3N / CH2Cl2 / 0.5 h / 0 - 5 °C 4: 2N NaOH / dioxane / 4 h / Ambient temperature 5: 32percent NH4OH / methanol / 6 h / sealed flask 6: 98 percent / Et3N / CH2Cl2 / 0.5 h / -10 - -5 °C 7: 86 percent / t-BuOK / 2-methyl-propan-2-ol / 3 h / Ambient temperature 8: RED-AL / toluene / 4 h / Ambient temperature View Scheme

1: 32percent NH4OH / methanol / 6 h / sealed flask 2: 98 percent / Et3N / CH2Cl2 / 0.5 h / -10 - -5 °C 3: 86 percent / t-BuOK / 2-methyl-propan-2-ol / 3 h / Ambient temperature 4: RED-AL / toluene / 4 h / Ambient temperature View Scheme

1: 98 percent / Et3N / CH2Cl2 / 0.5 h / -10 - -5 °C 2: 86 percent / t-BuOK / 2-methyl-propan-2-ol / 3 h / Ambient temperature 3: RED-AL / toluene / 4 h / Ambient temperature View Scheme

1: 61 percent / pyridine / 2 h / -10 °C 2: 84 percent / Et3N / CH2Cl2 / 0.5 h / 0 - 5 °C 3: 2N NaOH / dioxane / 4 h / Ambient temperature 4: 32percent NH4OH / methanol / 6 h / sealed flask 5: 98 percent / Et3N / CH2Cl2 / 0.5 h / -10 - -5 °C 6: 86 percent / t-BuOK / 2-methyl-propan-2-ol / 3 h / Ambient temperature 7: RED-AL / toluene / 4 h / Ambient temperature View Scheme

1.1: LDA / tetrahydrofuran / 0.5 h / -78 °C 1.2: tetrahydrofuran / 1 h / -78 °C 2.1: BH3 / tetrahydrofuran / 2 h / 60 °C 2.2: 60 percent / aq. HCl / 1 h / 60 °C 3.1: 56 percent / 1,1-(azodicarbonyl)dipiperidine; PBu3 / tetrahydrofuran / 40 °C 4.1: Et3N / CH2Cl2 / 40 °C 5.1: MeOH / Heating View Scheme

1: 84 percent / Et3N / CH2Cl2 / 0.5 h / 0 - 5 °C 2: 2N NaOH / dioxane / 4 h / Ambient temperature 3: 32percent NH4OH / methanol / 6 h / sealed flask 4: 98 percent / Et3N / CH2Cl2 / 0.5 h / -10 - -5 °C 5: 86 percent / t-BuOK / 2-methyl-propan-2-ol / 3 h / Ambient temperature 6: RED-AL / toluene / 4 h / Ambient temperature View Scheme

1: 2N NaOH / dioxane / 4 h / Ambient temperature 2: 32percent NH4OH / methanol / 6 h / sealed flask 3: 98 percent / Et3N / CH2Cl2 / 0.5 h / -10 - -5 °C 4: 86 percent / t-BuOK / 2-methyl-propan-2-ol / 3 h / Ambient temperature 5: RED-AL / toluene / 4 h / Ambient temperature View Scheme

1: MCPBA / CH2Cl2 / 0 deg C, 1.5 h, then RT, 24 h 2: 1.) NaOH / 1.) H2O, 70 deg C; 2.) H2O, 70 deg C, 2.5 h 3: 61 percent / pyridine / 2 h / -10 °C 4: 84 percent / Et3N / CH2Cl2 / 0.5 h / 0 - 5 °C 5: 2N NaOH / dioxane / 4 h / Ambient temperature 6: 32percent NH4OH / methanol / 6 h / sealed flask 7: 98 percent / Et3N / CH2Cl2 / 0.5 h / -10 - -5 °C 8: 86 percent / t-BuOK / 2-methyl-propan-2-ol / 3 h / Ambient temperature 9: RED-AL / toluene / 4 h / Ambient temperature View Scheme