triethylamine in dichloromethane Ambient temperature;

1: 5-fluoro-1H-imidazole-4-carboxylic acid ethyl ester With N-ethyl-N,N-diisopropylamine T=-12°C; 0.25 h; 2: chloromethyl methyl ether T=-12 - 20°C;

lithium borohydride T=0°C; 1.5 h;

1: 39.2 percent / 50percent HBF4 / NaNO2 / H2O / 4 h / -60 - -40 °C / Irradiation 2: 1) aq.NaNO2 / 1) 2N HCl (ice-cold) 2) 10percent Na2CO3 (ice-cold) 3: 65.5 percent / formamidinesulfinic acid (FASA) / NEt3 / methanol; H2O / 20 h / 45 - 50 °C 4: 53 percent / 50percent HBF4 / aq.NaNO2 / 3 h / -60 - -40 °C / Irradiation 5: 81 percent / NEt3 / CH2Cl2 / 2 h / Ambient temperature 6: NaBH4 / propan-1-ol / Ambient temperature View Scheme

1: 53 percent / 50percent HBF4 / aq.NaNO2 / 3 h / -60 - -40 °C / Irradiation 2: 81 percent / NEt3 / CH2Cl2 / 2 h / Ambient temperature 3: NaBH4 / propan-1-ol / Ambient temperature View Scheme

1: 81 percent / NEt3 / CH2Cl2 / 2 h / Ambient temperature 2: NaBH4 / propan-1-ol / Ambient temperature View Scheme

1: 65.5 percent / formamidinesulfinic acid (FASA) / NEt3 / methanol; H2O / 20 h / 45 - 50 °C 2: 53 percent / 50percent HBF4 / aq.NaNO2 / 3 h / -60 - -40 °C / Irradiation 3: 81 percent / NEt3 / CH2Cl2 / 2 h / Ambient temperature 4: NaBH4 / propan-1-ol / Ambient temperature View Scheme

1: 1) aq.NaNO2 / 1) 2N HCl (ice-cold) 2) 10percent Na2CO3 (ice-cold) 2: 65.5 percent / formamidinesulfinic acid (FASA) / NEt3 / methanol; H2O / 20 h / 45 - 50 °C 3: 53 percent / 50percent HBF4 / aq.NaNO2 / 3 h / -60 - -40 °C / Irradiation 4: 81 percent / NEt3 / CH2Cl2 / 2 h / Ambient temperature 5: NaBH4 / propan-1-ol / Ambient temperature View Scheme

lithium aluminium tetrahydride in diethyl ether; diethylene glycol dimethyl ether T=-78 - 20°C;