triethylamine in methanol; water T=40°C; 2 h;

1: pyridine / dichloromethane / 20 °C 2: triethylamine / 1,4-dioxane / 24 h / 70 °C 3: water / 1,4-dioxane / 16 h / 40 °C / pH ~ 9 - 10 View Scheme

1.1: triethylamine / water; methanol / 2 h / 40 °C 2.1: toluene-4-sulfonic acid; hydrogen / palladium on activated charcoal / methanol / 3.83 h / 50 °C / 37503.8 Torr 2.2: 50 - 65 °C View Scheme

1: triethylamine / water; methanol / 2 h / 40 °C 2: toluene-4-sulfonic acid / toluene / 0.5 h / 50 °C / Reflux 3: hydrogen / 5 palladium on charcoal / toluene / 2 h / 30 °C / 26252.6 Torr View Scheme