benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine in dichloromethane T=20°C; 64 h;

1: thionyl chloride / dichloromethane; N,N-dimethyl-formamide / 12 h / 20 °C 2: AlCl3, aluminium chloride / dichloromethane / 1 h / 0 °C 3: AlCl3, aluminium chloride / dichloromethane / 12 h / 20 °C / Inert atmosphere 4: boron trifluoride diethyl etherate; triethylsilane / dichloromethane; diethyl ether; acetonitrile / 16 h / 20 °C / Inert atmosphere View Scheme

1.1: isopropylmagnesium chloride / tetrahydrofuran / -30 - 20 °C / Inert atmosphere; Large scale reaction 1.2: 0 °C / Inert atmosphere; Large scale reaction 1.3: 10 - 20 °C / Large scale reaction 2.1: sodium hydride / tetrahydrofuran; mineral oil / 0 - 20 °C / Inert atmosphere; Large scale reaction 2.2: 20 - 50 °C / Inert atmosphere; Large scale reaction 3.1: Pearlman's catalyst; hydrogen / ethyl acetate / 18 h / 2327.23 Torr / Large scale reaction 4.1: 1,1'-carbonyldiimidazole / ethyl acetate / 2 h / 10 - 20 °C / Inert atmosphere; Large scale reaction 4.2: 30 °C / Inert atmosphere; Large scale reaction 5.1: sodium tetrahydroborate; BF3*THF / tetrahydrofuran / 20 - 37 °C / Inert atmosphere; Large scale reaction View Scheme

1: hydrogenchloride / water 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / N,N-dimethyl-formamide / Heating View Scheme

1: With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine in acetonitrile 2: With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl-4',4',5',5'-tetramethyl-1,3,2-dioxaborolane in 2-methyl tetrahydrofuran 3: With hydrogenchloride; sodium periodate in 2-methyl tetrahydrofuran; water