1: triethylamine / ethyl acetate / 0.42 h / -15 °C 2: triethylamine / ethyl acetate / 0.25 h / -15 °C 3: hydrogenchloride / water; ethyl acetate / 0.5 h / 15 - 25 °C 4: sodium hydroxide; tri-n-butylmethylammonium chloride / water / 2 h / 20 - 25 °C / |Large scale 5: ammonium hydroxide / methanol / 3 h / 40 °C / |Large scale 6: dichloromethane; isopropyl alcohol / 5 h / |Large scale 7: triethylamine; carbonic acid dimethyl ester / 0.5 h / 4 - 10 °C / |Large scale 8: potassium tert-butylate / isopropyl alcohol; tert-butyl alcohol / 1 h / 20 °C / |Large scale 9: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 0.25 h / 10 °C / |Large scale 10: acetone / 1 h / 0 - 5 °C / |Large scale 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: 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: ethyl acetate / 16 h View Scheme