in dichloromethane 2 h; Ambient temperature;

1: 75 percent / PdCl2(PPh3)2 / tetrahydrofuran / 24 h / 110 °C 2: CuSO4, NaBH4 / ethanol; H2O / 3 h / 0 °C 3: 1) conc. HCl, NaNO2, 2) NaN3, NaOAc / 1) H2O, 0 deg C, 1 h, 2) water, 0 deg C, 1 h 4: 90 percent / CH2Cl2 / 2 h / Ambient temperature View Scheme

1: 75 percent / PdCl2(PPh3)2 / tetrahydrofuran / 24 h / 110 °C 2: CuSO4, NaBH4 / ethanol; H2O / 3 h / 0 °C 3: 1) conc. HCl, NaNO2, 2) NaN3, NaOAc / 1) H2O, 0 deg C, 1 h, 2) water, 0 deg C, 1 h 4: 90 percent / CH2Cl2 / 2 h / Ambient temperature View Scheme

1: 1) conc. HCl, NaNO2, 2) NaN3, NaOAc / 1) H2O, 0 deg C, 1 h, 2) water, 0 deg C, 1 h 2: 90 percent / CH2Cl2 / 2 h / Ambient temperature View Scheme

1: CuSO4, NaBH4 / ethanol; H2O / 3 h / 0 °C 2: 1) conc. HCl, NaNO2, 2) NaN3, NaOAc / 1) H2O, 0 deg C, 1 h, 2) water, 0 deg C, 1 h 3: 90 percent / CH2Cl2 / 2 h / Ambient temperature View Scheme