1: 90 percent / NaOH / aq. ethanol / 2 h / Heating 2: 50 percent / H2O / Hog Kidney acylase, pH 7.5 3: 100 percent / 11M aq. HCl / H2O / 3 h / Heating View Scheme

1: aq. NaOH 2: (enzymatic racemate resolution) View Scheme

1.1: water; sodium hydroxide / 3 h / 50 - 65 °C 2.1: hydrogenchloride / water / 5 h / pH 5.0 / |Reflux 3.1: sodium hydroxide / water / 11 h / pH 7.5-10 4.1: thionyl chloride / tetrahydrofuran / 8 h / 20 °C 5.1: pyridine / ethyl acetate / 14 h / -10 °C / |Inert atmosphere; |Large scale 6.1: O-propargylquinidine / toluene / 0.17 h / -60 °C / |Inert atmosphere 6.2: 12 h / -60 °C / |Inert atmosphere 6.3: 12 h / 20 °C View Scheme

1.1: water; sodium hydroxide / 3 h / 50 - 65 °C 2.1: hydrogenchloride / water / 5 h / pH 5.0 / |Reflux 3.1: sodium hydroxide / water / 11 h / pH 7.5-10 4.1: thionyl chloride / tetrahydrofuran / 8 h / 20 °C 5.1: pyridine / ethyl acetate / 14 h / -10 °C / |Inert atmosphere; |Large scale 6.1: O-propargylquinidine / toluene / 0.17 h / -60 °C / |Inert atmosphere 6.2: 12 h / -60 °C / |Inert atmosphere 6.3: 12 h / 20 °C View Scheme

1: water; sodium hydroxide / 3 h / 50 - 65 °C 2: hydrogenchloride / water / 5 h / pH 5.0 / |Reflux 3: sodium hydroxide / water / 11 h / pH 7.5-10 View Scheme

sodium hydride in N,N-dimethyl-formamide T=60°C; 3 h;

potassium tert-butylate in 1,4-dioxane T=100°C;

in N,N-dimethyl-formamide

sodium hydroxide in ethanol 2 h; Heating;

potassium hydroxide in ethanol