1: 95.5 percent / pyridine / CH2Cl2 / Ambient temperature 2: 55.6 percent / BF3*Et2O / CH2Cl2 / 1.) -78 deg C, 1 h, 2.) RT, overnight 3: 100 percent / H2, triethylamine / 10percent Pd/C / 12 h / Ambient temperature 4: 71 percent / NaHCO3 / CHCl3 / 0.33 h View Scheme

boron trifluoride diethyl etherate in dichloromethane 24 h; Ambient temperature;

1: 68 percent / pyridine / CH2Cl2 / 12 h / Ambient temperature 2: 86 percent / H2 / 10percent Pd/C / ethyl acetate / 0.67 h / 2585.7 Torr 3: 69 percent / aq. NaHCO3 / CHCl3 / 0.33 h / Ambient temperature 4: 50 percent / BF3*Et2O / CH2Cl2 / 24 h / Ambient temperature View Scheme

sodium hydrogencarbonate in chloroform 0.333333 h;

1: 1.) methanesulfonic acid, NaNO2, 2.) aq. sodium azide / 1.) H2O, 5 deg C, 24 h, 2.) H2O, 5 deg C 2: 89 percent / KOH / methanol / 1 h / Ambient temperature 3: thionyl chloride / 5 h / Heating 4: 95 percent / pyridine / CH2Cl2 / Ambient temperature 5: 51 percent / BF3*Et2O / CH2Cl2 / 1.) -78 deg C, 1 h, 2.) RT, overnight 6: 5 mg / H2, triethylamine / 10percent Pd/C / 2 h / Ambient temperature 7: 71 percent / NaHCO3 / CHCl3 / 0.33 h View Scheme

1: thionyl chloride / 5 h / Heating 2: 95 percent / pyridine / CH2Cl2 / Ambient temperature 3: 51 percent / BF3*Et2O / CH2Cl2 / 1.) -78 deg C, 1 h, 2.) RT, overnight 4: 5 mg / H2, triethylamine / 10percent Pd/C / 2 h / Ambient temperature 5: 71 percent / NaHCO3 / CHCl3 / 0.33 h View Scheme

1: 95 percent / pyridine / CH2Cl2 / Ambient temperature 2: 51 percent / BF3*Et2O / CH2Cl2 / 1.) -78 deg C, 1 h, 2.) RT, overnight 3: 5 mg / H2, triethylamine / 10percent Pd/C / 2 h / Ambient temperature 4: 71 percent / NaHCO3 / CHCl3 / 0.33 h View Scheme

1: 89 percent / KOH / methanol / 1 h / Ambient temperature 2: thionyl chloride / 5 h / Heating 3: 95 percent / pyridine / CH2Cl2 / Ambient temperature 4: 51 percent / BF3*Et2O / CH2Cl2 / 1.) -78 deg C, 1 h, 2.) RT, overnight 5: 5 mg / H2, triethylamine / 10percent Pd/C / 2 h / Ambient temperature 6: 71 percent / NaHCO3 / CHCl3 / 0.33 h View Scheme

1: 55.6 percent / BF3*Et2O / CH2Cl2 / 1.) -78 deg C, 1 h, 2.) RT, overnight 2: 100 percent / H2, triethylamine / 10percent Pd/C / 12 h / Ambient temperature 3: 71 percent / NaHCO3 / CHCl3 / 0.33 h View Scheme

1: 1.) conc. HCl, NaNO2, 2.) aq. sodium azide / 1.) H2O, from 0 to 5 deg C, 1 h, 2.) H2O 2: 93 percent / KOH / methanol / 1 h / Ambient temperature 3: thionyl chloride / 5 h / Heating 4: 95.5 percent / pyridine / CH2Cl2 / Ambient temperature 5: 55.6 percent / BF3*Et2O / CH2Cl2 / 1.) -78 deg C, 1 h, 2.) RT, overnight 6: 100 percent / H2, triethylamine / 10percent Pd/C / 12 h / Ambient temperature 7: 71 percent / NaHCO3 / CHCl3 / 0.33 h View Scheme