1: 86 percent / ephedrine*HCl-LiAlH4 / diethyl ether / 2 h / -78 °C 2: 76 percent / sodium acetate / 4 h / 80 - 85 °C 3: p-acetamidobenzenesulfonyl azide, triethylamine / acetonitrile / 2 h / Ambient temperature 4: 73 percent / 1N NaOH / H2O / 1 h / Ambient temperature 5: 70 percent / copper(II)acetylacetonate / dioxane / 2 h / Heating 6: 91 percent / zinc dust / diethyl ether; acetic acid / 5 h / Ambient temperature 7: 89 percent / thionyl chloride / 1) 1h room temperature 2) 1h 35-40 deg C 8: 1) pyridine 2) aq. NH3 / 1) toluene, 30 deg C 2) 0 deg C, 2d View Scheme

sodium tetrahydroborate in methanol T=38 - 60°C; 1.16667 h;

1: sodium tetrahydroborate / methanol / 1.17 h / 38 - 60 °C 2: triethylamine / 1.3 h / 95 °C View Scheme