1: 96 percent / H2 / 10percent Pd/C / methanol; H2O / 16 h / pH <2 2: 81 percent / 0.25 h / 65 °C 3: 1.) N,N-bis(trimethylsilyl)trifluoroacetamide, pyridine, 2.) SnCl4 / 1.) CH3CN, room temperature, overnight, 2.) CH3CN, 1,2-dichloroethane, -45 deg C to -35 deg C, 0.75 h 4: 1.) NaOCH3, 2.) NaBH4 / 1.) CH3OH, 1 h, 2.) H2O, C2H5OH, 25 deg C, 0.5 h View Scheme

1: 75 percent / concd HCl, SnCl2*2H2O / ethanol / 2.5 h / 60 °C 2: 96 percent / H2 / 10percent Pd/C / methanol; H2O / 16 h / pH <2 3: 81 percent / 0.25 h / 65 °C 4: 1.) N,N-bis(trimethylsilyl)trifluoroacetamide, pyridine, 2.) SnCl4 / 1.) CH3CN, room temperature, overnight, 2.) CH3CN, 1,2-dichloroethane, -45 deg C to -35 deg C, 0.75 h 5: 1.) NaOCH3, 2.) NaBH4 / 1.) CH3OH, 1 h, 2.) H2O, C2H5OH, 25 deg C, 0.5 h View Scheme

sodium tetrahydroborate; sodium methylate 1.) CH3OH, 1 h, 2.) H2O, C2H5OH, 25 deg C, 0.5 h; Yield given. Multistep reaction;

1: 1.) N,N-bis(trimethylsilyl)trifluoroacetamide, pyridine, 2.) SnCl4 / 1.) CH3CN, room temperature, overnight, 2.) CH3CN, 1,2-dichloroethane, -45 deg C to -35 deg C, 0.75 h 2: 1.) NaOCH3, 2.) NaBH4 / 1.) CH3OH, 1 h, 2.) H2O, C2H5OH, 25 deg C, 0.5 h View Scheme

1: 81 percent / 0.25 h / 65 °C 2: 1.) N,N-bis(trimethylsilyl)trifluoroacetamide, pyridine, 2.) SnCl4 / 1.) CH3CN, room temperature, overnight, 2.) CH3CN, 1,2-dichloroethane, -45 deg C to -35 deg C, 0.75 h 3: 1.) NaOCH3, 2.) NaBH4 / 1.) CH3OH, 1 h, 2.) H2O, C2H5OH, 25 deg C, 0.5 h View Scheme