1.1: hydrogen / Pd(OH)2 on carbon / ethanol / 760 Torr 2.1: oxalyl chloride; DMF / CH2Cl2 / 0 - 20 °C 2.2: Bu4NBH4 / CH2Cl2 / -78 °C 3.1: 84 percent / CBr4; Ph3P / CH2Cl2 / 0 - 20 °C View Scheme

<b>Multi-step reaction with 2 steps<br /> </b>1: Rh₂(OAc)4 / tetrahydrofuran; H₂O / Heating<br />2: i-Pr₂NEt / tetrahydrofuran / 0 &deg;C<br /> <br /> &nbsp;

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '605301', constants.ctx, '0')">N-ethyl-N,N-diisopropylamine</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '102391', constants.ctx, '0')">tetrahydrofuran</a> <br />T=0&deg;C;&nbsp;<br /> &nbsp;

<b>Multi-step reaction with 4 steps<br /> </b>1: DMAP / toluene / Heating<br />2: p-toluenesulfonylazide; Et₃N / acetonitrile / 0 - 20 &deg;C<br />3: Rh₂(OAc)4 / tetrahydrofuran; H₂O / Heating<br />4: i-Pr₂NEt / tetrahydrofuran / 0 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 5 steps<br /> </b>1: MgCl₂; Et₃N / acetonitrile<br />2: DMAP / toluene / Heating<br />3: p-toluenesulfonylazide; Et₃N / acetonitrile / 0 - 20 &deg;C<br />4: Rh₂(OAc)4 / tetrahydrofuran; H₂O / Heating<br />5: i-Pr₂NEt / tetrahydrofuran / 0 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 4 steps<br /> </b>1: lithium perchlorate / toluene / 5 h / Reflux<br />2: triethylamine; 4-Acetylaminobenzenesulfonyl Azide / acetonitrile / 4 h / 20 &deg;C / Cooling with ice<br />3: water / dirhodium tetraacetate / tetrahydrofuran / 12 h / 90 &deg;C<br />4: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 6.5 h / 20 &deg;C / Cooling with ice<br /> <br /> &nbsp;