1.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / 25 °C / Inert atmosphere 1.2: 1.5 h / 25 °C / Inert atmosphere 1.3: pH 5 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetone / 8 h / 25 °C / Inert atmosphere 3.1: sodium iodide; cerium(III) chloride heptahydrate / acetonitrile / 2 h / 80 - 85 °C View Scheme

Stage #1: <b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '4123663', constants.ctx, '0')">diisobutylaluminium hydride</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '635760', constants.ctx, '0')">toluene</a> <br />T=-65 - -60&deg;C;&nbsp;1&nbsp;h;&nbsp;&nbsp;Inert atmosphere;&nbsp;<br />Stage #2: <b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1098229', constants.ctx, '0')">methanol</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '635760', constants.ctx, '0')">toluene</a> <br />T=25&deg;C;&nbsp;1&nbsp;h;&nbsp;<br /> <br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 8 h / 0 - 25 &deg;C / Inert atmosphere<br />2.1: triethylamine; hydrogen / palladium on carbon / ethyl acetate / 2 h / 25 &deg;C / 1471.14 Torr<br />3.1: diisobutylaluminium hydride / toluene / 1 h / -65 - -60 &deg;C / Inert atmosphere<br />3.2: 1 h / 25 &deg;C<br /> <br /> &nbsp;