1: sodium cyanoborohydride, acetic acid / methanol 2: TFA, triethylsilane / CH2Cl2 / 1 h / Ambient temperature View Scheme

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '3587189', constants.ctx, '0')">hydrogen</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '11378922', constants.ctx, '0')">palladium on activated charcoal</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '102391', constants.ctx, '0')">tetrahydrofuran</a> <br />P=2068.6&nbsp;Torr;&nbsp;0.5&nbsp;h;&nbsp;<br /> &nbsp;

<b>Multi-step reaction with 5 steps<br /> </b>1: 85 percent / aq. K₂CO₃, Pd(OAc)2 / acetone / 6 h / Heating<br />2: 89 percent / KMnO₄ / pyridine; H₂O / 1 h / Heating<br />3: oxalyl chloride, DMF / CH₂Cl₂ <br />4: 1.) n-BuLi / 1.) hexane, RT, 5 min, 2.) THF, hexane, RT, overnight<br />5: H₂ / 10percent Pd/C / tetrahydrofuran / 0.5 h / 2068.6 Torr<br /> <br /> &nbsp;

<b>Multi-step reaction with 5 steps<br /> </b>1: 85 percent / aq. K₂CO₃, Pd(OAc)2 / acetone / 6 h / Heating<br />2: 89 percent / KMnO₄ / pyridine; H₂O / 1 h / Heating<br />3: oxalyl chloride, DMF / CH₂Cl₂ <br />4: 1.) n-BuLi / 1.) hexane, RT, 5 min, 2.) THF, hexane, RT, overnight<br />5: H₂ / 10percent Pd/C / tetrahydrofuran / 0.5 h / 2068.6 Torr<br /> <br /> &nbsp;