1: 95 percent / SOCl2 / 24 h / Ambient temperature 2: 70 percent / (NH4)2CO3 / H2O; nitromethane / 96 h / 50 °C 3: 89 percent / TFA / 24 h / Ambient temperature 4: 75.8 percent / 1N NaOH / 24 h / Ambient temperature View Scheme

1: 70 percent / (NH4)2CO3 / H2O; nitromethane / 96 h / 50 °C 2: 89 percent / TFA / 24 h / Ambient temperature 3: 75.8 percent / 1N NaOH / 24 h / Ambient temperature View Scheme

1: 1.) NaNO2, 2N H2SO4; 2.) KBr, NaNO2, 3N H2SO4 / 1.) 50percent CH3COOH, r.t., 24 h; 2.) 50percent CH3COOH, 0-5 deg C, 1 h 2: 95 percent / SOCl2 / 24 h / Ambient temperature 3: 70 percent / (NH4)2CO3 / H2O; nitromethane / 96 h / 50 °C 4: 89 percent / TFA / 24 h / Ambient temperature 5: 75.8 percent / 1N NaOH / 24 h / Ambient temperature View Scheme

sodium hydroxide; trifluoroacetic acid Multistep reaction;

sodium hydroxide; Dowex 50 (H+, 50-100 mesh); sodium cyanoborohydride 1.) water, room temperature, pH 7.0; Yield given. Multistep reaction. Yields of byproduct given;

1: 1.) molecular sieves, sodium acetate, catecholborane / 1.) CH2Cl2, -15 - 0 deg C, 1 h.; 2.) CH2Cl2 2: 1.) TFA; 2.) 1M NaOH View Scheme