1: 94 percent / AcOH / 5 h / 150 °C 2: 82 percent / H2 / Pd-C / tetrahydrofuran; methanol / 10 h / 760 Torr View Scheme

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1098214', constants.ctx, '0')">hydrogenchloride</a>;&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, '102391', constants.ctx, '0')">tetrahydrofuran</a>;&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 2 steps<br /> </b>1: 1.) LHMDS / 1.) THF, room temperature, 50 min, 2.) toluene, 2 h.<br />2: 76 percent / NaBH₄, HCl / tetrahydrofuran; ethanol / 2 h / 0 &deg;C<br /> <br /> &nbsp;