hydrogenchloride; hydrogen; palladium on activated charcoal in ethanol 2 h;

1: dimethylformamide 2: sodium borohydride, boron trifluoride etherate / tetrahydrofuran / 5 h / Heating 3: hydrogen, conc. hydrochloric acid / 10percent palladium-charcoal / ethanol / 2 h View Scheme

1: thionyl chloride 2: dimethylformamide 3: sodium borohydride, boron trifluoride etherate / tetrahydrofuran / 5 h / Heating 4: hydrogen, conc. hydrochloric acid / 10percent palladium-charcoal / ethanol / 2 h View Scheme

1: sodium borohydride, boron trifluoride etherate / tetrahydrofuran / 5 h / Heating 2: hydrogen, conc. hydrochloric acid / 10percent palladium-charcoal / ethanol / 2 h View Scheme

1: lithium aluminium hydride / tetrahydrofuran / 2 h / Heating 2: thionyl chloride 3: dimethylformamide 4: sodium borohydride, boron trifluoride etherate / tetrahydrofuran / 5 h / Heating 5: hydrogen, conc. hydrochloric acid / 10percent palladium-charcoal / ethanol / 2 h View Scheme

1: 88 percent / potassium carbonate, potassium iodide / acetone / 18 h / Heating 2: lithium aluminium hydride / tetrahydrofuran / 2 h / Heating 3: thionyl chloride 4: dimethylformamide 5: sodium borohydride, boron trifluoride etherate / tetrahydrofuran / 5 h / Heating 6: hydrogen, conc. hydrochloric acid / 10percent palladium-charcoal / ethanol / 2 h View Scheme