potassium carbonate in N,N-dimethyl-formamide T=70°C; Etherification; 4 h;

potassium carbonate in N,N-dimethyl-formamide T=0 - 20°C; 16 h;

N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate T=20°C; 35 h; Inert atmosphere;

1.1: sodium bis(2-methoxyethoxy)aluminium dihydride / tetrahydrofuran / 4 h / 0 - 5 °C / Inert atmosphere 1.2: Inert atmosphere; Cooling 2.1: hydrogen / palladium 10 on activated carbon / ethyl acetate; methanol / 5 h / 50 °C / Inert atmosphere 3.1: potassium carbonate / N,N-dimethyl-formamide / 20 h / 20 °C 3.2: 20 °C 4.1: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 6 h / 20 - 40 °C / Inert atmosphere 5.1: potassium carbonate / dichloromethane; methanol / 30 h / 20 °C 6.1: hydrogen / palladium(II) oxide hydrate / ethyl acetate / 40 h / 20 °C View Scheme

1.1: sodium bis(2-methoxyethoxy)aluminium dihydride / tetrahydrofuran / 4 h / 0 - 5 °C / Inert atmosphere 1.2: Inert atmosphere; Cooling 2.1: hydrogen / palladium 10 on activated carbon / ethyl acetate; methanol / 5 h / 50 °C / Inert atmosphere 3.1: CHIRAL PAK.(R). IC (250 X 4.6) mm, 5μ column / methanol / 25 °C / Resolution of racemate View Scheme

potassium hydroxide in pyridine; diethylene glycol T=120°C; Ring cleavage; 6 h;