alcalase CLEAreg;; 1,8-diazabicyclo[5.4.0]undec-7-ene in tert-butyl alcohol T=37°C; 144 h; Resolution of racemateEnzymatic reaction; optical yield given as percent eeenantioselective reaction;

sodium hydroxide in water T=0 - 20°C; 1 h;

sodium hydroxide in 1,4-dioxane pH 10;

dipyridinium dichromate in N,N-dimethyl-formamide 24 h;

1: 89 percent / imidazole / dimethylformamide / 24 h / Ambient temperature 2: 87 percent / triethylamine, 4-(N,N-dimethylamino)pyridine / CH2Cl2 / 5 h / -15 - 23 °C 3: 82 percent / sodium hydride / tetrahydrofuran / 3 h / Ambient temperature 4: 88 percent / hydrogen / Pd/C / ethyl acetate / 4 h 5: 93 percent / tetrabutylammonium fluoride monohydrate / tetrahydrofuran / 1 h / Ambient temperature 6: 71 percent / pyridinium dichromate / dimethylformamide / 24 h View Scheme

1: 87 percent / triethylamine, 4-(N,N-dimethylamino)pyridine / CH2Cl2 / 5 h / -15 - 23 °C 2: 82 percent / sodium hydride / tetrahydrofuran / 3 h / Ambient temperature 3: 88 percent / hydrogen / Pd/C / ethyl acetate / 4 h 4: 93 percent / tetrabutylammonium fluoride monohydrate / tetrahydrofuran / 1 h / Ambient temperature 5: 71 percent / pyridinium dichromate / dimethylformamide / 24 h View Scheme

1: 82 percent / sodium hydride / tetrahydrofuran / 3 h / Ambient temperature 2: 88 percent / hydrogen / Pd/C / ethyl acetate / 4 h 3: 93 percent / tetrabutylammonium fluoride monohydrate / tetrahydrofuran / 1 h / Ambient temperature 4: 71 percent / pyridinium dichromate / dimethylformamide / 24 h View Scheme

in hydrogenchloride; methanol; dichloromethane; toluene

1: 93 percent / tetrabutylammonium fluoride monohydrate / tetrahydrofuran / 1 h / Ambient temperature 2: 71 percent / pyridinium dichromate / dimethylformamide / 24 h View Scheme

1: 87 percent / 1 M NaOH / aq. ethanol / 6 h / Ambient temperature 2: 94 percent / 0.17 h / 160 °C 3: 97 percent 4: 53 percent / 6 N aq. HCl / 2 h / Heating 5: 100 percent / 0.5 N aq. NaOH / dioxane / pH 10 View Scheme