1,4-diaza-bicyclo[2.2.2]octane in 1,4-dioxane T=60°C; 7 h;

1: 85 percent / AcONH4 / acetic acid / 3 h / 110 °C 2: 98 percent / LiAlH4 / CH2Cl2; diethyl ether / 0.5 h / Ambient temperature 3: 48 percent / aq. HCl / methanol / 3 h / Heating 4: 74 percent / ethanol / 1 h / 5 - 20 °C 5: 75 percent / 55 - 70 °C 6: 98 percent / MeONa / methanol / 12 h / 60 °C 7: 93 percent / K2CO3 / acetone / 12 h / 41 °C 8: 82 percent / LiAlH4 / CH2Cl2; diethyl ether / 0.5 h / Ambient temperature 9: 68 percent / diazabicyclooctane / dioxane / 7 h / 60 °C View Scheme

1: 98 percent / LiAlH4 / CH2Cl2; diethyl ether / 0.5 h / Ambient temperature 2: 48 percent / aq. HCl / methanol / 3 h / Heating 3: 74 percent / ethanol / 1 h / 5 - 20 °C 4: 75 percent / 55 - 70 °C 5: 98 percent / MeONa / methanol / 12 h / 60 °C 6: 93 percent / K2CO3 / acetone / 12 h / 41 °C 7: 82 percent / LiAlH4 / CH2Cl2; diethyl ether / 0.5 h / Ambient temperature 8: 68 percent / diazabicyclooctane / dioxane / 7 h / 60 °C View Scheme

1: 48 percent / aq. HCl / methanol / 3 h / Heating 2: 74 percent / ethanol / 1 h / 5 - 20 °C 3: 75 percent / 55 - 70 °C 4: 98 percent / MeONa / methanol / 12 h / 60 °C 5: 93 percent / K2CO3 / acetone / 12 h / 41 °C 6: 82 percent / LiAlH4 / CH2Cl2; diethyl ether / 0.5 h / Ambient temperature 7: 68 percent / diazabicyclooctane / dioxane / 7 h / 60 °C View Scheme

1: 74 percent / ethanol / 1 h / 5 - 20 °C 2: 75 percent / 55 - 70 °C 3: 98 percent / MeONa / methanol / 12 h / 60 °C 4: 93 percent / K2CO3 / acetone / 12 h / 41 °C 5: 82 percent / LiAlH4 / CH2Cl2; diethyl ether / 0.5 h / Ambient temperature 6: 68 percent / diazabicyclooctane / dioxane / 7 h / 60 °C View Scheme

1: 75 percent / 55 - 70 °C 2: 98 percent / MeONa / methanol / 12 h / 60 °C 3: 93 percent / K2CO3 / acetone / 12 h / 41 °C 4: 82 percent / LiAlH4 / CH2Cl2; diethyl ether / 0.5 h / Ambient temperature 5: 68 percent / diazabicyclooctane / dioxane / 7 h / 60 °C View Scheme

1: 93 percent / K2CO3 / acetone / 12 h / 41 °C 2: 82 percent / LiAlH4 / CH2Cl2; diethyl ether / 0.5 h / Ambient temperature 3: 68 percent / diazabicyclooctane / dioxane / 7 h / 60 °C View Scheme

1: 82 percent / LiAlH4 / CH2Cl2; diethyl ether / 0.5 h / Ambient temperature 2: 68 percent / diazabicyclooctane / dioxane / 7 h / 60 °C View Scheme

1: 98 percent / MeONa / methanol / 12 h / 60 °C 2: 93 percent / K2CO3 / acetone / 12 h / 41 °C 3: 82 percent / LiAlH4 / CH2Cl2; diethyl ether / 0.5 h / Ambient temperature 4: 68 percent / diazabicyclooctane / dioxane / 7 h / 60 °C View Scheme