1: 1.) p-toluenesulfonic acid, 2.) 10percent NaOH / 1.) toluene, reflux, 3 h, 2.) reflux, 2 h 2: 37 percent / 1.) N-bromosuccinimide, 2.) NH3 / 1.) CCl4, reflux, 48 h, 2.) THF, 3 h 3: 16 percent / NH3 / tetrahydrofuran / 3 h 4: 65 percent / 1 M NH4OH / 1 h / 70 °C 5: 59 percent / H2, Raney nickel W-5 / ethanol / 16 h / 3040 Torr / Ambient temperature View Scheme

1: 1.) p-toluenesulfonic acid, 2.) 10percent NaOH / 1.) toluene, reflux, 3 h, 2.) reflux, 2 h 2: 37 percent / 1.) N-bromosuccinimide, 2.) NH3 / 1.) CCl4, reflux, 48 h, 2.) THF, 3 h 3: 16 percent / NH3 / tetrahydrofuran / 3 h 4: 65 percent / 1 M NH4OH / 1 h / 70 °C 5: 59 percent / H2, Raney nickel W-5 / ethanol / 16 h / 3040 Torr / Ambient temperature 6: 54 percent / 6 M HCl / 2 h / Heating View Scheme

1: 5.67 g / p-TSA / toluene / Heating 2: 92 percent / NBS; AIBN / CCl4 / 10 h / Heating View Scheme

phosphorus; hydrogen iodide Heating;

1: aq. HI, phosphorus / Heating 2: polyphosphoric acid View Scheme

1.1: 5.67 g / p-TSA / toluene / Heating 2.1: 92 percent / NBS; AIBN / CCl4 / 10 h / Heating 3.1: 78 percent / NaN3 / ethanol; H2O / 8 h / Heating 4.1: H2 / Ru(II)-(S)-BINAP / methanol / 20 h / 50 °C / 10343 Torr 4.2: CoCl2*6H2O; NaBH4 / methanol / 0.5 h 4.3: aq. 6N HCl / 10 h / 100 °C View Scheme

1.1: 5.67 g / p-TSA / toluene / Heating 2.1: 92 percent / NBS; AIBN / CCl4 / 10 h / Heating 3.1: 78 percent / NaN3 / ethanol; H2O / 8 h / Heating 4.1: H2 / Ru(II)-(S)-BINAP / methanol / 20 h / 50 °C / 10343 Torr 4.2: CoCl2*6H2O; NaBH4 / methanol / 0.5 h 4.3: aq. 6N HCl / 10 h / 100 °C View Scheme