sodium hydrogencarbonate in ethanol; water T=60°C; 2 h;

trimethylsilyl trifluoromethanesulfonate; dimethylsulfide borane complex; potassium hydrogencarbonate 1.) dichloromethane, -20 - -10 deg C, 0.2 h, 2.) ethanol, water, 55-65 deg C, 1 h; Yield given. Multistep reaction;

1: 95 percent / perchloric acid 2: 1.) BH3-SMe2, trimethylsilyl trifluoromethanesulfonate, 2.) potassium hydroden carbonate / 1.) dichloromethane, -20 - -10 deg C, 0.2 h, 2.) ethanol, water, 55-65 deg C, 1 h View Scheme

1.1: pyridine; sulfuryl dichloride / dichloromethane / -30 - -20 °C 2.1: perchloric acid / 18 h 3.1: dimethylsulfide borane complex; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / -30 - -20 °C 3.2: 12 h / 20 °C 3.3: 2 h / 55 - 65 °C View Scheme

1.1: toluene-4-sulfonic acid / acetone / 2 h / |Reflux; |Large scale 2.1: ethanol / 2 h / 20 °C 2.2: 1 h / 0 - 10 °C 3.1: pyridine; sulfuryl dichloride / dichloromethane / -30 - -20 °C 4.1: perchloric acid / 18 h 5.1: dimethylsulfide borane complex; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / -30 - -20 °C 5.2: 12 h / 20 °C 5.3: 2 h / 55 - 65 °C View Scheme

1.1: toluene-4-sulfonic acid / acetone / 2 h / |Reflux; |Large scale 2.1: ethanol / 2 h / 20 °C 2.2: 1 h / 0 - 10 °C 3.1: pyridine; sulfuryl dichloride / dichloromethane / -30 - -20 °C 4.1: perchloric acid / 18 h 5.1: dimethylsulfide borane complex; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / -30 - -20 °C 5.2: 12 h / 20 °C 5.3: 2 h / 55 - 65 °C View Scheme

1.1: ethanol / 2 h / 20 °C 1.2: 1 h / 0 - 10 °C 2.1: pyridine; sulfuryl dichloride / dichloromethane / -30 - -20 °C 3.1: perchloric acid / 18 h 4.1: dimethylsulfide borane complex; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / -30 - -20 °C 4.2: 12 h / 20 °C 4.3: 2 h / 55 - 65 °C View Scheme

1.1: 97 percent / MgBr2*OEt2 / acetonitrile; various solvent(s) / 16 h / 55 °C 2.1: ethanolamine; Pd/C / ethanol / 3 h / Heating 2.2: 77 percent / H2SO4 3.1: various solvent(s) 4.1: Et3N / various solvent(s) 5.1: various solvent(s) / 15 h / 111 - 112 °C / 2625.21 - 3375.27 Torr 6.1: AcOH; MeSO3H / various solvent(s) / 15 h / 20 °C 7.1: NH2CH2CH2OH; Pd/C / ethanol / 3 h / Heating View Scheme

sodium azide; ammonium chloride; trimethylphosphane 1.) ethanol, water, 70-75 deg C, 18 h, 2.) acetonitrile, <38 deg C, 2 h; Yield given. Multistep reaction;

1: 1.) sodium azide, ammonium chloride, 2.) trimethylphosphine / 1.) ethanol, water, 70-75 deg C, 18 h, 2.) acetonitrile, <38 deg C, 2 h 2: sodium azide, ammonium chloride / dimethylformamide / 18 h / 70 - 80 °C 3: 0.98 kg / sodium bicarbonate / hexane / 1 h 4: 1.) hydrogen, 2.) phophoric acid / 1.) Raney nickel / 1.) ethanol, 16 h, 2.) ethanol, 55 65 deg C View Scheme