1: N,N-di-isopropyl-3-(2-hydroxy-5-methylphenyl)-3-phenylpropyl amine hydrobromide With sodium hydroxide in dichloromethane; water 2: L-(+)-tartaric acid in ethanol T=60 - 85°C;

1: (+/-)-N,N-diisopropyl-3-(2-hydroxy-5-methylphenyl)-3-phenyl-propanamide With sodium bis(2-methoxyethoxy)aluminium dihydride in toluene T=5 - 40°C; 6 h; Cooling with ice; 2: L-(+)-tartaric acid in ethanol T=0 - 70°C; Reflux;

1: N,N-diisopropyl-3-(2-hydroxy-5-methylphenyl)-3-phenylpropylamine hydrochloride With sodium carbonate; sodium hydroxide in dichloromethane; water T=20°C; 1 h; 2: L-(+)-tartaric acid in methanol; acetone 1 h; Reflux;

in ethanol T=60 - 85°C;

in ethanol T=0 - 70°C;

1: tolterodine hydrobromide With potassium hydroxide in water; ethyl acetate 0.25 - 0.5 h; 2: L-(+)-tartaric acid in ethanol; ethyl acetate T=0°C; 5 - 17 h; Product distribution / selectivity;

1: (+/-)-N,N-diisopropyl-3-(2-hydroxy-5-methylphenyl)-3-phenyl-propanamide With sodium bis(2-methoxyethoxy)aluminium dihydride in toluene T=70°C; 6.08333 h; Inert atmosphereCooling with ice; 2: With sodium hydroxide in acetone; toluene T=40 - 60°C; 0.25 h; 3: L-(+)-tartaric acid in methanol T=0°C; Reflux; Product distribution / selectivity;

in ethanol T=25 - 30°C; 0.5 h; Resolution of racemate; Product distribution / selectivity;

in water; isopropyl alcohol T=20 - 65°C; Resolution of racemateReflux; Purification / work up;

1.1: FeCl3·6H2O / dichloromethane / 24 h / |Reflux 2.1: sodium hydroxide / dichloromethane; water / 1 h / 40 °C 3.1: triethylamine / water / 2 h / 0 °C 4.1: acetonitrile / 12 h / |Reflux 5.1: sodium hydroxide / methanol; water / 4 h / |Reflux 5.2: 1 h / 20 °C 6.1: sodium hydroxide; sodium carbonate / dichloromethane; water / 1 h / 20 °C 6.2: 1 h / |Reflux View Scheme