1: H2, 1.0 M Na2CO3(aq.) / 5percent Pd/C / 3.5 h / 3102.9 Torr / Ambient temperature 2: tetrahydrofuran; diethyl ether / 1.) 1 h, ice cooled, 2.) 2 h, ambient temperature View Scheme

1: H2, 1.0 M Na2CO3(aq.) / 5percent Pd/C / 3.5 h / 3102.9 Torr / Ambient temperature 2: tetrahydrofuran; diethyl ether / 1.) 1 h, ice cooled, 2.) 2 h, ambient temperature 3: 71 percent / N,N'-dicyclohexylcarbodiimide / dimethylformamide / 20 h / Ambient temperature View Scheme

1: SOCl2 / tetrahydrofuran / 0.08 h / Heating 2: Hunig's base / tetrahydrofuran / -20 - 20 °C 3: 1.) H2, 2.) HCl / 10percent Pd/C / 1.) methanol, 40 deg C, 1 atm, 2.) isopropanol, -30 deg C 4: 64 percent / 1,8-bis(dimethylamino)naphthalene, dicyclohexylcarbodiimide / tetrahydrofuran; dimethylformamide / 3 h / Ambient temperature 5: 1.) HCl, 2.) NH3 / 1.) EtOH, RT, 1.5 h, 2.) EtOH, 1 h, RT 6: 70 percent / H2 / 10percent Pd/C / methanol / 40 °C 7: methanol; tetrahydrofuran / 0.5 h / -40 °C View Scheme

1: SOCl2 / tetrahydrofuran / 0.08 h / Heating 2: 7.22 g / Huenig's base / tetrahydrofuran / -20 - 20 °C View Scheme

thionyl chloride Multistep reaction;

sulfuric acid 12 h; Heating;

1: 95 percent / H2SO4 / 12 h / Heating 2: H2 / Pd/C / dimethylformamide / 18 h / 20 °C View Scheme

1: H2, 1.0 M Na2CO3(aq.) / 5percent Pd/C / 3.5 h / 3102.9 Torr / Ambient temperature 2: 2.5 h / ice-bath View Scheme

1: H2, 1.0 M Na2CO3(aq.) / 5percent Pd/C / 3.5 h / 3102.9 Torr / Ambient temperature 2: tetrahydrofuran; diethyl ether / 1.) 1 h, ice cooled, 2.) 2 h, ambient temperature 3: 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride / dimethylformamide / 40 °C 4: TFA / CH2Cl2 5: EDC / dimethylformamide / 40 °C 6: H2 / 5percent Pd/C / dimethylformamide / 2 h / 3102.9 Torr / Ambient temperature View Scheme

sulfuric acid in diethyl ether T=20°C; 36 h;