1: 88 percent / NaHCO3 / tetrahydrofuran; H2O / 16 h / Ambient temperature 2: 71.4 percent / H2 / 10percent Pd/C / ethanol / 18 h / 3040 Torr 3: 1.) borane*THF complex 2.) HCl / 1.) THF, 60 deg C, 20 h 2.) methanol, reflux, 2 h View Scheme

1: 71.4 percent / H2 / 10percent Pd/C / ethanol / 18 h / 3040 Torr 2: 1.) borane*THF complex 2.) HCl / 1.) THF, 60 deg C, 20 h 2.) methanol, reflux, 2 h View Scheme

1: 83 percent / thionyl chloride / 4 h / Heating 2: 88 percent / NaHCO3 / tetrahydrofuran; H2O / 16 h / Ambient temperature 3: 71.4 percent / H2 / 10percent Pd/C / ethanol / 18 h / 3040 Torr 4: 1.) borane*THF complex 2.) HCl / 1.) THF, 60 deg C, 20 h 2.) methanol, reflux, 2 h View Scheme