1.1: imidazole / dimethylformamide / 1 h / 20 °C 2.1: 3.76 g / tetrabutylammonium iodide; NaH / dimethylformamide / 3 h / 0 °C 3.1: 72 percent / sodium acetate / PdCl2 / acetic acid; H2O / 3.5 h / 50 °C 4.1: 87 percent / AcOH; TBAF / tetrahydrofuran / 8 h / 20 °C 5.1: H2 / 10 percent Pd/C / acetic acid; ethanol; H2O / 45 h / 20 °C 5.2: 53 percent / HCl / H2O View Scheme

1.1: imidazole / dimethylformamide / 1 h / 20 °C 2.1: 3.76 g / tetrabutylammonium iodide; NaH / dimethylformamide / 3 h / 0 °C 3.1: 72 percent / sodium acetate / PdCl2 / acetic acid; H2O / 3.5 h / 50 °C 4.1: 87 percent / AcOH; TBAF / tetrahydrofuran / 8 h / 20 °C 5.1: H2 / 10 percent Pd/C / acetic acid; ethanol; H2O / 45 h / 20 °C 5.2: 53 percent / HCl / H2O View Scheme

Stage #1: <b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '742035', constants.ctx, '0')">trifluoroacetic acid</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '102551', constants.ctx, '0')">1,4-dioxane</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '3587155', constants.ctx, '0')">water</a> <br />T=20&deg;C;&nbsp;11&nbsp;h;&nbsp;<br />Stage #2: <b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '11343078', constants.ctx, '0')">sodium tetrahydroborate</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1718733', constants.ctx, '0')">ethanol</a> <br />T=0&deg;C;&nbsp;2&nbsp;h;&nbsp;<br /> &nbsp;

<b>Multi-step reaction with 10 steps<br /> </b>1.1: 175 g / acetic acid; H₂O / 16 h / 60 &deg;C<br />2.1: CH₂Cl₂; pyridine / 1 h / -15 &deg;C<br />3.1: 179 g / CH₂Cl₂; pyridine / 20 h / -15 - 20 &deg;C<br />4.1: NaOMe / methanol; tetrahydrofuran; CH₂Cl₂ / 3 h / 20 &deg;C<br />4.2: 78 percent / t-BuOK / dimethylformamide; tetrahydrofuran / 6 h / 0 - 20 &deg;C<br />5.1: 3.70 g / NH₄Cl; NaN₃ / dimethylformamide; H₂O / 2 h / 80 &deg;C<br />6.1: 3.84 g / n-tetrabutylammonium iodide; NaH / dimethylformamide / 2.5 h / 0 &deg;C<br />7.1: 50 percent / 3 percent HCl / 18 h / 20 &deg;C<br />8.1: 44.1 g / pyridine / CH₂Cl₂ / 1.6 h / -60 &deg;C<br />9.1: PPh₃ / CH₂Cl₂ / 4 h / 20 - 45 &deg;C<br />9.2: K₂CO₃ / H₂O; tetrahydrofuran; methanol / 96 h / 20 &deg;C<br />9.3: 27.3 g / tetrahydrofuran; methanol; H₂O / 7 h / 0 &deg;C<br />10.1: TFA / dioxane; H₂O / 11 h / 20 &deg;C<br />10.2: 71 percent / NaBH₄ / ethanol / 2 h / 0 &deg;C<br /> <br /> &nbsp;