1: LiAlH4 2: pyridinium chlorochromate View Scheme

1: 97 percent / conc. H2SO4, conc. HNO3 / 0.5 h / 0 °C 2: 91 percent / HCO2NH4 / Pd/C / methanol / 6 h / Heating 3: 99 percent / CuCl2, t-BuONO / acetonitrile / 0.5 h / 65 °C 4: 93 percent / LiBH4 / tetrahydrofuran / 1.) 0 deg C, 2 h, 2.) reflux, 4 h 5: 1.) DMSO, oxalyl chloride, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 15 min, 2.) -78 deg C, 45 min, -78 deg C to room temperature, 10 min View Scheme

1: 97 percent / conc. H2SO4, conc. HNO3 / 0.5 h / 0 °C 2: 91 percent / HCO2NH4 / Pd/C / methanol / 6 h / Heating 3: 99 percent / CuCl2, t-BuONO / acetonitrile / 0.5 h / 65 °C 4: 93 percent / LiBH4 / tetrahydrofuran / 1.) 0 deg C, 2 h, 2.) reflux, 4 h View Scheme