1: hydrogenchloride; water / acetonitrile / 4 h / -10 °C 2: sodium tetrahydroborate; diethyl methoxy borane; methanol / ethyl acetate; tetrahydrofuran / 5 h / -80 - -75 °C / Inert atmosphere View Scheme

<b>Multi-step reaction with 2 steps<br /> </b>1.1: dichloromethane / 3.25 h / 15 - 20 &deg;C<br />2.1: zinc oxide / toluene / 2 h / 25 - 30 &deg;C / Inert atmosphere<br />2.2: 12 h<br /> <br /> &nbsp;

<b>Multi-step reaction with 8 steps<br /> </b>1.1: diisobutylaluminium hydride / toluene / 2 h / -60 - -50 &deg;C / Inert atmosphere<br />1.2: 0.5 h / -50 - 30 &deg;C<br />2.1: manganese(IV) oxide / toluene / 24 h / 25 - 30 &deg;C<br />3.1: lithium hexamethyldisilazane / hexane; tetrahydrofuran / 1 h / -35 - -15 &deg;C<br />3.2: 1 h / -80 - -75 &deg;C<br />4.1: sodium hydroxide; water / tetrahydrofuran / 24 h / 20 - 30 &deg;C<br />4.2: pH 1.5 - 2<br />4.3: 20 &deg;C<br />5.1: hydrogenchloride; water / dichloromethane / 0 - 30 &deg;C / pH 2 - 2.5<br />6.1: potassium iodide / N,N-dimethyl-formamide / 0.75 h / 25 - 65 &deg;C / Inert atmosphere<br />6.2: 0.5 h / 60 - 65 &deg;C<br />6.3: 0.5 h / 60 - 65 &deg;C<br />7.1: dichloromethane / 3.25 h / 15 - 20 &deg;C<br />8.1: zinc oxide / toluene / 2 h / 25 - 30 &deg;C / Inert atmosphere<br />8.2: 12 h<br /> <br /> &nbsp;

Stage #1: <a href="#" onclick="return RXDsubstances(event, this, '1758845', constants.ctx, '0')">propanedioic acid monoethyl ester</a> <b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '8128140', constants.ctx, '0')">zinc oxide</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '635760', constants.ctx, '0')">toluene</a> <br />T=25 - 30&deg;C;&nbsp;2&nbsp;h;&nbsp;&nbsp;Inert atmosphere;&nbsp;<br />Stage #2: <a href="#" onclick="return RXDsubstances(event, this, '22983024', constants.ctx, '0')">C₃₂H₃₆FN₃O₂Si</a> &nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '102391', constants.ctx, '0')">tetrahydrofuran</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '635760', constants.ctx, '0')">toluene</a> <br />12&nbsp;h;&nbsp;<br /> <br /> &nbsp;

<b>Multi-step reaction with 9 steps<br /> </b>1.1: isopropyl alcohol / 25 - 82 &deg;C<br />2.1: diisobutylaluminium hydride / toluene / 2 h / -60 - -50 &deg;C / Inert atmosphere<br />2.2: 0.5 h / -50 - 30 &deg;C<br />3.1: manganese(IV) oxide / toluene / 24 h / 25 - 30 &deg;C<br />4.1: lithium hexamethyldisilazane / hexane; tetrahydrofuran / 1 h / -35 - -15 &deg;C<br />4.2: 1 h / -80 - -75 &deg;C<br />5.1: sodium hydroxide; water / tetrahydrofuran / 24 h / 20 - 30 &deg;C<br />5.2: pH 1.5 - 2<br />5.3: 20 &deg;C<br />6.1: hydrogenchloride; water / dichloromethane / 0 - 30 &deg;C / pH 2 - 2.5<br />7.1: potassium iodide / N,N-dimethyl-formamide / 0.75 h / 25 - 65 &deg;C / Inert atmosphere<br />7.2: 0.5 h / 60 - 65 &deg;C<br />7.3: 0.5 h / 60 - 65 &deg;C<br />8.1: dichloromethane / 3.25 h / 15 - 20 &deg;C<br />9.1: zinc oxide / toluene / 2 h / 25 - 30 &deg;C / Inert atmosphere<br />9.2: 12 h<br /> <br /> &nbsp;

<b>Multi-step reaction with 6 steps<br /> </b>1.1: lithium hexamethyldisilazane / hexane; tetrahydrofuran / 1 h / -35 - -15 &deg;C<br />1.2: 1 h / -80 - -75 &deg;C<br />2.1: sodium hydroxide; water / tetrahydrofuran / 24 h / 20 - 30 &deg;C<br />2.2: pH 1.5 - 2<br />2.3: 20 &deg;C<br />3.1: hydrogenchloride; water / dichloromethane / 0 - 30 &deg;C / pH 2 - 2.5<br />4.1: potassium iodide / N,N-dimethyl-formamide / 0.75 h / 25 - 65 &deg;C / Inert atmosphere<br />4.2: 0.5 h / 60 - 65 &deg;C<br />4.3: 0.5 h / 60 - 65 &deg;C<br />5.1: dichloromethane / 3.25 h / 15 - 20 &deg;C<br />6.1: zinc oxide / toluene / 2 h / 25 - 30 &deg;C / Inert atmosphere<br />6.2: 12 h<br /> <br /> &nbsp;