1: diisobutylaluminum hydride (DIBAH) / tetrahydrofuran / -50 °C 2: 4-dimethylaminopyridine (DMAP), pyridine / CH2Cl2 3: 93 percent / H2, pyridine / Pd/C / ethyl acetate 4: 82 percent / 2 N aq. HCl / tetrahydrofuran 5: 33 percent / pyridinium dichromate (PDC), 4A molecular sieves / CH2Cl2 View Scheme

1: diisobutylaluminum hydride (DIBAH) / tetrahydrofuran / -50 °C 2: 4-dimethylaminopyridine (DMAP), pyridine / CH2Cl2 3: 93 percent / H2, pyridine / Pd/C / ethyl acetate 4: 82 percent / 2 N aq. HCl / tetrahydrofuran View Scheme

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '3764305', constants.ctx, '0')">pyridinium p-toluenesulfonate</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1730800', constants.ctx, '0')">dichloromethane</a> <br /> <br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1: H₂ / Pd/C / acetone; H₂O<br />2: 2 N aq. HCl / 80 &deg;C<br />3: 90 percent / pyridinium p-toluenesulfonate (PPTS) / CH₂Cl₂ <br /> <br /> &nbsp;