potassium hydroxide in 1,4-dioxane; water 1) 0 deg C, 1 h, 2) room temp., 4 h;

hydrogen; 10percent Pd/C in ethyl acetate

in dichloromethane T=0 - 20°C;

1: 44 percent / Et3N / tetrahydrofuran / 1) -5 deg C, 2 h, 2) room temp., overnight 2: 85 percent / NaN3 / acetonitrile / 36 h / Heating 3: 100 percent / triphenylphosphine, H2O / tetrahydrofuran / 4 h / Ambient temperature 4: 90 percent / KOH / H2O; dioxane / 1) 0 deg C, 1 h, 2) room temp., 4 h View Scheme

1: 100 percent / triphenylphosphine, H2O / tetrahydrofuran / 4 h / Ambient temperature 2: 90 percent / KOH / H2O; dioxane / 1) 0 deg C, 1 h, 2) room temp., 4 h View Scheme

1: 85 percent / NaN3 / acetonitrile / 36 h / Heating 2: 100 percent / triphenylphosphine, H2O / tetrahydrofuran / 4 h / Ambient temperature 3: 90 percent / KOH / H2O; dioxane / 1) 0 deg C, 1 h, 2) room temp., 4 h View Scheme

1: sodium azide / N,N-dimethyl-formamide / 20 °C 2: palladium on carbon; hydrogen / tetrahydrofuran 3: dichloromethane View Scheme

trifluoroacetic acid in dichloromethane T=20°C;

1: sodium hydroxide / tetrahydrofuran; toluene / 45 °C 2: hydrogenchloride; water / 1 h 3: potassium carbonate / water / 16.75 h / 20 °C View Scheme