1: With lithium aluminium tetrahydride in diethyl ether 96 h; Heating / reflux; 2: With water; acetic acid in diethyl ether pH=5; Product distribution / selectivity;

1: With lithium aluminium tetrahydride in diethyl ether 96 h; Heating / reflux; 2: With acetic acid in diethyl ether pH=5; 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=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-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;

1.1: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 6 h / 5 - 40 °C / Cooling with ice 1.2: 20 - 60 °C 2.1: ethanol / 0 - 70 °C View Scheme