1: 98 percent / quinoline, hydrogen / Lindlar catalyst / ethyl acetate / 3 h 2: 82 percent / xylene / Heating 3: 96 percent / hydrogen / 10percent Pd/C / ethyl acetate / Ambient temperature 4: LiAlH4 / tetrahydrofuran / Ambient temperature 5: pyridine / Ambient temperature 6: LiAlH4 / tetrahydrofuran / 2 h / Ambient temperature 7: p-TsOH*H2O / dioxane; H2O / 3 h / Heating View Scheme

1: 82 percent / xylene / Heating 2: 96 percent / hydrogen / 10percent Pd/C / ethyl acetate / Ambient temperature 3: LiAlH4 / tetrahydrofuran / Ambient temperature 4: pyridine / Ambient temperature 5: LiAlH4 / tetrahydrofuran / 2 h / Ambient temperature 6: p-TsOH*H2O / dioxane; H2O / 3 h / Heating View Scheme

1: 96 percent / hydrogen / 10percent Pd/C / ethyl acetate / Ambient temperature 2: LiAlH4 / tetrahydrofuran / Ambient temperature 3: pyridine / Ambient temperature 4: LiAlH4 / tetrahydrofuran / 2 h / Ambient temperature 5: p-TsOH*H2O / dioxane; H2O / 3 h / Heating View Scheme

1: pyridine / 6 h / 20 °C 2: LiAlH4 / tetrahydrofuran / 5 h / 0 °C View Scheme

Morus alba Methylation;

1: 80 percent / PPh3 / pyridine 2: 99 percent / n-BuLi; D2O 4: HCl 5: 4 percent / Morus alba View Scheme

toluene-4-sulfonic acid in 1,4-dioxane; water 3 h; Heating; Yield given;

1: LiAlH4 / tetrahydrofuran / Ambient temperature 2: pyridine / Ambient temperature 3: LiAlH4 / tetrahydrofuran / 2 h / Ambient temperature 4: p-TsOH*H2O / dioxane; H2O / 3 h / Heating View Scheme

potassium hydroxide

2: palladium; ethyl acetate / Hydrogenation 3: ethanolic KOH View Scheme