1: 81 percent / toluene / 12 h / Heating 2: 87 percent / H2, conc. HCl / 10percent Pd/C / ethanol / 12 h / 3102.9 Torr View Scheme

1: 75 percent / NaH / tetrahydrofuran / 24 h / Heating 2: 98 percent / hydrogen / Pd/C / ethanol / 24 h / 100 °C / 6080 Torr View Scheme

N-ethyl-N,N-diisopropylamine in tetrahydrofuran

1: NaH / tetrahydrofuran / 12 h / Ambient temperature 2: pyridine / 0 °C View Scheme

1: NaH / tetrahydrofuran / 3 h / 100 °C 2: aq. NaOH / tetrahydrofuran / 20 h / 20 °C View Scheme

1: 52 percent / potassium tert-butoxide / tetrahydrofuran / 13 h / Heating 2: 89 percent / pyridine / CH2Cl2 / 13 h / Ambient temperature View Scheme

1: 66 percent / NaH / tetrahydrofuran / 24 h / Heating 2: 97 percent / hydrogen / Pd/C / ethanol / 24 h / 100 °C / 6080 Torr View Scheme

sodium azide in N,N-dimethyl-formamide T=50°C; 12 h;

1: sodium azide / dimethylformamide / 12 h / 50 °C 2: 1.) PPh3, 2.) H2O / 1.) THF, RT, 12 h, 2.) RT, 12 h View Scheme

1: 81 percent / toluene / 12 h / Heating 2: 87 percent / H2, conc. HCl / 10percent Pd/C / ethanol / 12 h / 3102.9 Torr 3: 72 percent / pyridine / CH2Cl2 / 13 h / Ambient temperature 4: 90 percent / H2 / 10percent Pd/C / ethanol / 8 h / 2585.7 Torr 5: 48percent HBF4, NaNO2 / H2O / 0.17 h / 0 °C 6: NaOAc / 1,1,2-trichloro-1,2,2-trifluoro-ethane / 24 h View Scheme