1: 95 percent / acetonitrile / 90 h / Heating 2: 94 percent / tosyl azide, Et3N 3: 42 percent / NaH / 1,2-dimethoxy-ethane / 3 h / 20 °C 4: 94 percent / NH3 / methanol / 7 h / 90 - 95 °C 5: 85 percent / 90percent trifluoroacetic acid / 0.75 h / 20 °C View Scheme

1: 2-fluoromethyl pyridiniumtosylate; DIEA / CH2Cl2 / -30 - 0 °C 2: 5 percent Spectr. / CBr4 / methanol / 12 h / Heating View Scheme

hydrogenchloride 1.) acetonitrile, reflux 10 h, 2.) dioxane, water, room temperature, 6 h; Yield given. Multistep reaction. Yields of byproduct given;

1.1: potassium tert-butoxide / tetrahydrofuran / 0 - 20 °C 1.2: 82 percent / tetrahydrofuran / 7 h / 0 - 20 °C 2.1: 90 percent / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / 1 h / 20 °C 3.1: 100 percent / tetrahydrofuran / -78 °C View Scheme

sodium hydride in tetrahydrofuran; dimethyl sulfoxide T=-10 - 60°C; 4 h;

in tetrahydrofuran; N,N,N',N',N'',N''-hexamethylphosphoric triamide

in acetonitrile