1: With benzotriazol-1-ol; N'-(3-dimethylaminopropyl)-N-ethylcarbodiimide in N,N-dimethyl-formamide T=20°C; 24 h; 2: With acetic acid 3 h; Heating / reflux; Product distribution / selectivity;

1.1: 5 palladium on charcoal; hydrogen / ethanol / 48 h / 20 °C 2.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 24 h / 20 °C 2.2: 3 h / |Reflux View Scheme

1.1: thionyl chloride; N,N-dimethyl-formamide / tetrahydrofuran / 6 h / |Reflux 2.1: triethylamine / tetrahydrofuran / 2 h / 0 - 5 °C 2.2: 10 - 20 °C 3.1: sodium tetrahydroborate; boron trifluoride diethyl etherate / tetrahydrofuran / 0 - 20 °C / |Inert atmosphere 3.2: 0 °C / |Reflux 4.1: 5 palladium on charcoal; hydrogen / ethanol / 48 h / 20 °C 5.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 24 h / 20 °C 5.2: 3 h / |Reflux View Scheme

1.1: triethylamine / tetrahydrofuran / 2 h / 0 - 5 °C 1.2: 10 - 20 °C 2.1: sodium tetrahydroborate; boron trifluoride diethyl etherate / tetrahydrofuran / 0 - 20 °C / |Inert atmosphere 2.2: 0 °C / |Reflux 3.1: 5 palladium on charcoal; hydrogen / ethanol / 48 h / 20 °C 4.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 24 h / 20 °C 4.2: 3 h / |Reflux View Scheme

1.1: sodium tetrahydroborate; boron trifluoride diethyl etherate / tetrahydrofuran / 0 - 20 °C / |Inert atmosphere 1.2: 0 °C / |Reflux 2.1: 5 palladium on charcoal; hydrogen / ethanol / 48 h / 20 °C 3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 24 h / 20 °C 3.2: 3 h / |Reflux View Scheme

hydrogen; palladium on activated carbon in N,N-dimethyl-formamide T=20°C; 24 h; Product distribution / selectivity;