1: 66 percent / Cs2CO3 / dimethylformamide / 40 h / 70 °C 2: 80percent m-CPBA / CH2Cl2 / 4 h / Ambient temperature 3: 78 percent / aq. K2CO3 / methanol / 72 h / Ambient temperature 4: 48 percent / 1-methyl-2-pyrrolidinone / 16 h / 180 °C 5: 5 N HCl, H2 / Pd(OH)2/C / ethanol / 6 h / 40 °C / 2068.6 Torr 6: 1 N NaOH / dioxane / 18 h / Ambient temperature 7: 42 percent / DMAP / CH2Cl2 / 18 h / Ambient temperature 8: 85 percent / KOH / ethanol / 2 h / Ambient temperature 9: 1.) oxalyl chloride, DMSO, 2.) Et3N / 1.) CH2Cl2, -70 deg C, 20 min View Scheme

triethylamine in dichloromethane T=0 - 20°C; 6.25 h; Inert atmosphere;

1: With 1H-imidazole; iodine; triphenylphosphine in dichloromethane T=20°C; Reflux; 2: With 1,8-diazabicyclo[5.4.0]undec-7-ene in tetrahydrofuran 18 h; Reflux;

triethylamine in dichloromethane T=0 - 20°C; 16 h;

1: NaN3 / tetrabutylammonium bromide / CH2Cl2; H2O / 2 h / 0 °C 2: CH2Cl2 / 6 h / Heating View Scheme

1H-imidazole; iodine; triphenylphosphine in dichloromethane T=20°C; Inert atmosphere;

1: Et3N; diphenylphosphoryl azide / toluene / 3 h / Heating 2: 12.91 g / toluene / 16 h / 80 °C View Scheme

in toluene T=80°C; 16 h;

in dichloromethane 6 h; Heating; Yield given;

1: 66 percent / Cs2CO3 / dimethylformamide / 40 h / 70 °C 2: 80percent m-CPBA / CH2Cl2 / 4 h / Ambient temperature 3: 78 percent / aq. K2CO3 / methanol / 72 h / Ambient temperature 4: 48 percent / 1-methyl-2-pyrrolidinone / 16 h / 180 °C 5: 5 N HCl, H2 / Pd(OH)2/C / ethanol / 6 h / 40 °C / 2068.6 Torr 6: 1 N NaOH / dioxane / 18 h / Ambient temperature 7: 42 percent / DMAP / CH2Cl2 / 18 h / Ambient temperature 8: 85 percent / KOH / ethanol / 2 h / Ambient temperature 9: 1.) oxalyl chloride, DMSO, 2.) Et3N / 1.) CH2Cl2, -70 deg C, 20 min 10: n-BuLi / diethyl ether; tetrahydrofuran; hexane / 1.) -70 deg C, 20 min, 2.) -70 deg C, 2 h; -50 deg C, 30 min 11: KH / tetrahydrofuran / 1.) r.t., 20 min, 2.) r.t., 20 min 12: toluene / 2 h / Heating 13: H2 / PtO2 / ethyl acetate / 1 h / 2068.6 Torr 14: HCl / ethyl acetate / 1 h / 0 °C View Scheme