sodium tetrahydroborate; palladium on activated charcoal in methanol; water 2.5 h;

1: HNO3, Ac2O 2: H2 / PtO2 View Scheme

1: HF, Py 2: HNO3, Ac2O 3: H2 / PtO2 View Scheme

1: 66 percent / HNO3 / acetic anhydride / 1) 25 deg C, 20 min; 2) stirring, 4 h. 2: 100 percent / NaOH / H2O; methanol / 2 h / Heating 3: 59.5 percent / 2-chloro-1,1,2-trifluorotriethylamine / 1.5 h / 130 °C 4: 93 percent / 10percent Pd/C, NaBH4 / methanol; H2O / 2.5 h View Scheme

1: 59.5 percent / 2-chloro-1,1,2-trifluorotriethylamine / 1.5 h / 130 °C 2: 93 percent / 10percent Pd/C, NaBH4 / methanol; H2O / 2.5 h View Scheme

1: 100 percent / NaOH / H2O; methanol / 2 h / Heating 2: 59.5 percent / 2-chloro-1,1,2-trifluorotriethylamine / 1.5 h / 130 °C 3: 93 percent / 10percent Pd/C, NaBH4 / methanol; H2O / 2.5 h View Scheme