1: 90 percent / triethylamine, (N,N-dimethylamino)pyridine / CH2Cl2 / 0.5 h / 0 °C 2: 80 percent / Amberlyst A 26 (CO32-) / benzene / 12 h / Heating 3: 1) NaH (50percent in mineral oil) / 1) THF a) 0 deg C b) 1h room temperature 2) 1.5h, 0 deg C 4: 95 percent / N-iodosuccinimide / CHCl3 / 8 h / Ambient temperature 5: 95 percent / 2N HCl / methanol / 24 h / Ambient temperature 6: 88 percent / tri-n-butyltin hydride, azobis(isobutyronitrile) / benzene; methanol / 5 h / Heating View Scheme

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '906717', constants.ctx, '0')">lithium diisopropyl amide</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, '1730733', constants.ctx, '0')">hexane</a> <br />20&nbsp;h;&nbsp;&nbsp;Ambient temperature;&nbsp;<br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1: 89 percent / Br₂ / diethyl ether / 0.5 h / -40 &deg;C<br />2: 61 percent / formic acid / methanol / 0.08 h / 20 &deg;C<br />3: 94 percent / lithium aluminium hydride / diethyl ether / 0.75 h / -50 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 4 steps<br /> </b>1: 85 percent / Et₃N / Ru(II) complex from (1S,2S)-N-(pTs)-1,2-diPhethylenediamine / formic acid / 42 h / 20 &deg;C<br />2: 89 percent / Br₂ / diethyl ether / 0.5 h / -40 &deg;C<br />3: 61 percent / formic acid / methanol / 0.08 h / 20 &deg;C<br />4: 94 percent / lithium aluminium hydride / diethyl ether / 0.75 h / -50 &deg;C<br /> <br /> &nbsp;