1: 86 percent / H2 / 5percent Pd/C / methanol / 3 h / Ambient temperature 2: 90 percent / CH2Cl2 / 48 h / Ambient temperature 3: 1.) sodium hydride, DMSO, triphenylmethane / 1.) RT, 2.) 10 min 4: 86 percent / 10percent KOH / 1.5 h / Heating View Scheme

<b>Multi-step reaction with 2 steps<br /> </b>1.1: 92.8 percent / K₂CO₃ / acetonitrile / 3 h / 0 &deg;C<br />2.1: Mg / diethyl ether<br />2.2: 91 percent / diethyl ether / 3 h / Heating<br /> <br /> &nbsp;

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '3535220', constants.ctx, '0')">methylmagnesium bromide</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '3547232', constants.ctx, '0')">ammonium chloride</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, '1696894', constants.ctx, '0')">diethyl ether</a> <br /> <br /> <br /> &nbsp;

&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, '1696894', constants.ctx, '0')">diethyl ether</a> <br />&nbsp;1.) -20 deg C, 0.5 h, 2.) 0 deg C, 1 h;&nbsp;<br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1: HCl<br /> <br /> &nbsp;

Stage #1: <a href="#" onclick="return RXDsubstances(event, this, '969135', constants.ctx, '0')">methyl iodide</a> <b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '4948473', constants.ctx, '0')">magnesium</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1696894', constants.ctx, '0')">diethyl ether</a> <br />Metallation;&nbsp;<br />Stage #2: <a href="#" onclick="return RXDsubstances(event, this, '487027', constants.ctx, '0')">(S)-Pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester</a> &nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1696894', constants.ctx, '0')">diethyl ether</a> <br />Grignard reaction;&nbsp;3&nbsp;h;&nbsp;&nbsp;Heating;&nbsp;&nbsp;Further stages.;&nbsp;<br /> &nbsp;

<br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1.1: SOCl₂ / Heating<br />2.1: 92.8 percent / K₂CO₃ / acetonitrile / 3 h / 0 &deg;C<br />3.1: Mg / diethyl ether<br />3.2: 91 percent / diethyl ether / 3 h / Heating<br /> <br /> &nbsp;