pyridine in dichloromethane 6 h; Ambient temperature;

1: 43 percent / p-toluenesulfonic acid / hexane / 50 °C 2: 32 percent / toluene / 43 h / 80 °C 3: 82 percent / trichlorosilane, triethylamine / toluene / 1) room temperature, overnight 2) 4h 40 deg C 4: 76 percent / sodium acetate / 4 h / 80 - 85 °C 5: p-acetamidobenzenesulfonyl azide, triethylamine / acetonitrile / 2 h / Ambient temperature 6: 73 percent / 1N NaOH / H2O / 1 h / Ambient temperature 7: 70 percent / copper(II)acetylacetonate / dioxane / 2 h / Heating 8: 91 percent / zinc dust / diethyl ether; acetic acid / 5 h / Ambient temperature 9: 89 percent / thionyl chloride / 1) 1h room temperature 2) 1h 35-40 deg C 10: 1) pyridine 2) aq. NH3 / 1) toluene, 30 deg C 2) 0 deg C, 2d View Scheme

1: 32 percent / toluene / 43 h / 80 °C 2: 82 percent / trichlorosilane, triethylamine / toluene / 1) room temperature, overnight 2) 4h 40 deg C 3: 76 percent / sodium acetate / 4 h / 80 - 85 °C 4: p-acetamidobenzenesulfonyl azide, triethylamine / acetonitrile / 2 h / Ambient temperature 5: 73 percent / 1N NaOH / H2O / 1 h / Ambient temperature 6: 70 percent / copper(II)acetylacetonate / dioxane / 2 h / Heating 7: 91 percent / zinc dust / diethyl ether; acetic acid / 5 h / Ambient temperature 8: 89 percent / thionyl chloride / 1) 1h room temperature 2) 1h 35-40 deg C 9: 1) pyridine 2) aq. NH3 / 1) toluene, 30 deg C 2) 0 deg C, 2d View Scheme

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

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

1: 70 percent / copper(II)acetylacetonate / dioxane / 2 h / Heating 2: 91 percent / zinc dust / diethyl ether; acetic acid / 5 h / Ambient temperature 3: 89 percent / thionyl chloride / 1) 1h room temperature 2) 1h 35-40 deg C 4: 1) pyridine 2) aq. NH3 / 1) toluene, 30 deg C 2) 0 deg C, 2d View Scheme

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

1: 73 percent / 1N NaOH / H2O / 1 h / Ambient temperature 2: 70 percent / copper(II)acetylacetonate / dioxane / 2 h / Heating 3: 91 percent / zinc dust / diethyl ether; acetic acid / 5 h / Ambient temperature 4: 89 percent / thionyl chloride / 1) 1h room temperature 2) 1h 35-40 deg C 5: 1) pyridine 2) aq. NH3 / 1) toluene, 30 deg C 2) 0 deg C, 2d View Scheme

1: 82 percent / trichlorosilane, triethylamine / toluene / 1) room temperature, overnight 2) 4h 40 deg 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

1: 91 percent / zinc dust / diethyl ether; acetic acid / 5 h / Ambient temperature 2: 89 percent / thionyl chloride / 1) 1h room temperature 2) 1h 35-40 deg C 3: 1) pyridine 2) aq. NH3 / 1) toluene, 30 deg C 2) 0 deg C, 2d View Scheme