1: 88 percent / potassium carbonate, acetic acid / methanol / 0.75 h / 22 °C 2: 91 percent / H2 / palladium hydroxide on carbon / methanol / 44 h / 3102.9 Torr 3: trifluoroacetic acid/water (9/1) / 1 h / 22 °C 4: 49 percent / liquid ammonia, sodium / -78 °C View Scheme

<b>Multi-step reaction with 12 steps<br /> </b>1: 99 percent / H₂ / 10percent Pd/C / methanol / 3102.9 Torr<br />2: 56 percent / m-CPBA / CH₂Cl₂ / 0.28 h / Heating<br />3: 86 percent / KF / acetonitrile / 24 h / 22 &deg;C<br />4: 96 percent / dicyclohexylcarbodiimde, copper(I) chloride / acetonitrile / 16 h / 35 &deg;C<br />5: 84 percent / zinc dust, acetic acid / tetrahydrofuran / 0.25 h / 45 &deg;C<br />6: 81 percent / cerium(IV) ammonium nitrate, HNO₃ / ethanol / 0.25 h / -42 &deg;C<br />7: 80 percent / L-selectride / tetrahydrofuran / 2 h / -78 &deg;C<br />8: pyridine / 1 h / 0 &deg;C<br />9: 100 percent / sodium azide, ammonium chloride / dimethylformamide / 16 h / 22 &deg;C<br />10: 4 N HCl / dioxane / 96 h / 22 &deg;C<br />11: 554 mg / sodium acetate / 6.5 h / 50 &deg;C<br />12: 59 percent / SnCl₄ / CH₂Cl₂; acetonitrile / 16 h / 22 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 10 steps<br /> </b>1: 86 percent / KF / acetonitrile / 24 h / 22 &deg;C<br />2: 96 percent / dicyclohexylcarbodiimde, copper(I) chloride / acetonitrile / 16 h / 35 &deg;C<br />3: 84 percent / zinc dust, acetic acid / tetrahydrofuran / 0.25 h / 45 &deg;C<br />4: 81 percent / cerium(IV) ammonium nitrate, HNO₃ / ethanol / 0.25 h / -42 &deg;C<br />5: 80 percent / L-selectride / tetrahydrofuran / 2 h / -78 &deg;C<br />6: pyridine / 1 h / 0 &deg;C<br />7: 100 percent / sodium azide, ammonium chloride / dimethylformamide / 16 h / 22 &deg;C<br />8: 4 N HCl / dioxane / 96 h / 22 &deg;C<br />9: 554 mg / sodium acetate / 6.5 h / 50 &deg;C<br />10: 59 percent / SnCl₄ / CH₂Cl₂; acetonitrile / 16 h / 22 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 11 steps<br /> </b>1: 56 percent / m-CPBA / CH₂Cl₂ / 0.28 h / Heating<br />2: 86 percent / KF / acetonitrile / 24 h / 22 &deg;C<br />3: 96 percent / dicyclohexylcarbodiimde, copper(I) chloride / acetonitrile / 16 h / 35 &deg;C<br />4: 84 percent / zinc dust, acetic acid / tetrahydrofuran / 0.25 h / 45 &deg;C<br />5: 81 percent / cerium(IV) ammonium nitrate, HNO₃ / ethanol / 0.25 h / -42 &deg;C<br />6: 80 percent / L-selectride / tetrahydrofuran / 2 h / -78 &deg;C<br />7: pyridine / 1 h / 0 &deg;C<br />8: 100 percent / sodium azide, ammonium chloride / dimethylformamide / 16 h / 22 &deg;C<br />9: 4 N HCl / dioxane / 96 h / 22 &deg;C<br />10: 554 mg / sodium acetate / 6.5 h / 50 &deg;C<br />11: 59 percent / SnCl₄ / CH₂Cl₂; acetonitrile / 16 h / 22 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 10 steps<br /> </b>1: 86 percent / KF / acetonitrile / 24 h / 22 &deg;C<br />2: 96 percent / dicyclohexylcarbodiimde, copper(I) chloride / acetonitrile / 16 h / 35 &deg;C<br />3: 84 percent / zinc dust, acetic acid / tetrahydrofuran / 0.25 h / 45 &deg;C<br />4: 81 percent / cerium(IV) ammonium nitrate, HNO₃ / ethanol / 0.25 h / -42 &deg;C<br />5: 80 percent / L-selectride / tetrahydrofuran / 2 h / -78 &deg;C<br />6: pyridine / 1 h / 0 &deg;C<br />7: 100 percent / sodium azide, ammonium chloride / dimethylformamide / 16 h / 22 &deg;C<br />8: 4 N HCl / dioxane / 96 h / 22 &deg;C<br />9: 554 mg / sodium acetate / 6.5 h / 50 &deg;C<br />10: 59 percent / SnCl₄ / CH₂Cl₂; acetonitrile / 16 h / 22 &deg;C<br /> <br /> &nbsp;