1: With borane-THF in tetrahydrofuran T=0°C; 3.33 h; Heating / reflux; 2: With hydrogenchloride in tetrahydrofuran; water 3 h; Heating / reflux; 3: With sodium hydroxide in tetrahydrofuran; water

1: With formic acid in water T=95 - 100°C; 15 - 20 h; 2: With sodium hydroxide in water T=10°C; pH=9.5 - 10;

1: 1,5-dibromo-pentane With iodine; magnesium in tetrahydrofuran 2 h; Reflux; 2: 2-(4-benzyloxy-phenyl)-3-dimethylamino-propionic acid methyl ester in tetrahydrofuran T=0 - 30°C; 3: With water; ammonium chloride in tetrahydrofuran

1: 2-(4-benzyloxy-phenyl)-N,N-dimethyl-acetamide With isopropylmagnesium chloride in tetrahydrofuran T=5 - 35°C; 1 h; 2: cyclohexanone in tetrahydrofuran T=5 - 35°C; 0.283333 - 1 h; 3: With sodium hydroxide; water; sodium bis(2-methoxyethoxy)aluminium dihydride; citric acid Product distribution / selectivity; more than 3 stages;

1.1: potassium carbonate / tetrabutylammomium bromide / toluene / 5.6 - 6 h / Reflux 2.1: lithium perchlorate / toluene / 2.5 h / 5 - 30 °C 3.1: iodine; magnesium / tetrahydrofuran / 2 h / Reflux 3.2: 0 - 30 °C View Scheme

1.1: thionyl chloride / 5 - 6 h / 5 - 20 °C 2.1: potassium carbonate / tetrabutylammomium bromide / toluene / 5.6 - 6 h / Reflux 3.1: lithium perchlorate / toluene / 2.5 h / 5 - 30 °C 4.1: iodine; magnesium / tetrahydrofuran / 2 h / Reflux 4.2: 0 - 30 °C View Scheme

1.1: lithium perchlorate / toluene / 2.5 h / 5 - 30 °C 2.1: iodine; magnesium / tetrahydrofuran / 2 h / Reflux 2.2: 0 - 30 °C View Scheme

1: With hydrogenchloride in methanol; water pH=5; 2: With hydrogen; Raney nickel; methanol washed in methanol; water T=50°C; P=750.075 Torr; 2 h; 3: With ammonia in methanol; water pH=9.5; Product distribution / selectivity;

palladium monocarbide in ethanol