methylamine in ethanol T=20°C;

1: CH2Cl2 / 2 h / 0 °C 2: 78 percent / pyridine, 4-dimethylaminopyridine / CH2Cl2 / 3 h / 20 °C 3: 54 percent / trimethylsilyl trifluoromethanesulfonate / acetonitrile / 0.25 h / -35 °C 4: 78 percent / methylamine / ethanol / 20 °C View Scheme

1: 78 percent / pyridine, 4-dimethylaminopyridine / CH2Cl2 / 3 h / 20 °C 2: 54 percent / trimethylsilyl trifluoromethanesulfonate / acetonitrile / 0.25 h / -35 °C 3: 78 percent / methylamine / ethanol / 20 °C View Scheme

1: 54 percent / trimethylsilyl trifluoromethanesulfonate / acetonitrile / 0.25 h / -35 °C 2: 78 percent / methylamine / ethanol / 20 °C View Scheme

1: mercuric sulfate, 5 mM aq. H2SO4 / acetone / 5 h / Ambient temperature 2: CH2Cl2 / 2 h / 0 °C 3: 78 percent / pyridine, 4-dimethylaminopyridine / CH2Cl2 / 3 h / 20 °C 4: 54 percent / trimethylsilyl trifluoromethanesulfonate / acetonitrile / 0.25 h / -35 °C 5: 78 percent / methylamine / ethanol / 20 °C View Scheme