1: 85 percent / NaN3 / dimethylformamide / 120 °C 2: Dowex 50(H+) / methanol 3: H2 / Pd/C / methanol View Scheme

1: 85 percent / NaN3 / dimethylformamide / 120 °C 2: Dowex 50(H+) / methanol View Scheme

1: 85 percent / NaN3 / dimethylformamide / 120 °C 2: 85 percent / SnCl2 / methanol 3: 90 percent / ethyldiisopropylamine / dimethylformamide / 0 deg C to 20 deg C 4: 90 percent / Bu4NF / tetrahydrofuran / 20 °C View Scheme

ethyl trifluoromethanesulphonate; anhydrous tetramethylammonium chloride 1.) CH2Cl2, 0 deg C, 2 h, 2a.) CH3CN, 20 deg C, 30 min, 2b.) 40 deg C, 4 d, 2c.) 80 deg C, 2 d; Yield given. Multistep reaction. Yields of byproduct given;

anhydrous tetramethylammonium chloride 1.) CH2Cl2, 0 deg C, 2 h, 2a.) CH3CN, CH2Cl2, 20 deg C, 30 min, 2b.) 40 deg C, 4 d, 2c.) 80 deg C, 2 d; Yield given. Multistep reaction. Yields of byproduct given;