1: 88 percent / dicyclohexylcarbodiimide / tetrahydrofuran / Heating; overnight 2: 84 percent / tetrahydrofuran / 60 °C / overnight 3: 90 percent / SOCl2 / dimethylformamide / 0.75 h / 45 °C 4: H2 / 10percent Pd/C / acetic acid / 18 h / 55 °C / 2585.7 Torr 5: 78 percent / LiAlH4 / tetrahydrofuran; diethyl ether / 16 h / Heating View Scheme

1: 88 percent / dicyclohexylcarbodiimide / tetrahydrofuran / Heating; overnight 2: 84 percent / tetrahydrofuran / 60 °C / overnight 3: 90 percent / SOCl2 / dimethylformamide / 0.75 h / 45 °C 4: H2 / 10percent Pd/C / acetic acid / 18 h / 55 °C / 2585.7 Torr View Scheme

thionyl chloride in N,N-dimethyl-formamide T=50°C; overnight;

palladium on activated charcoal; sodium carbonate Hydrogenation;

1: diethyl ether 2: palladium/charcoal; aqueous Na2CO3 / Hydrogenation View Scheme

1: 72 percent 2: 40 percent / SOCl2 / dimethylformamide / 50 °C / overnight View Scheme

hydrogenchloride; potassium hydroxide 1.) acetic anhydride, 100 deg C, O.5 h, then 120-130 deg C, 3 h; 2.) aq. ethanol, reflux, 5 h; Yield given. Multistep reaction;

1: 88 percent / dicyclohexylcarbodiimide / tetrahydrofuran / Heating; overnight 2: 86 percent / acetonitrile 3: 1.) SOCl2 / 1.) benzene, reflux, 1.5 h; 2.) hexamethylphosphoramide, 180 deg C 4: H2 / 10percent Pd/C / acetic acid / 18 h / 55 °C / 2585.7 Torr 5: 60 percent / LiAlH4 / tetrahydrofuran; diethyl ether / Heating View Scheme