1: 95 percent / pyridinium dichromate / CH2Cl2 / 5 h / Ambient temperature 2: 98 percent / aq. HCl / methanol / 2 h / Ambient temperature 3: 54 percent / D-camphor-10-sulfonic acid / benzene / 3 h / Heating 4: 80 percent / LiAlH4 / tetrahydrofuran / 0.5 h / 0 °C 5: 83 percent / DMSO, oxalyl chloride, NEt3 / 1) CH2Cl2, -78 deg C, 1 h, 2) 0 deg C, 1 h 6: 1) n-butyllithium / 1) THF, hexane, -78 deg C, 4 min, 2) -78 deg C, 30 min 7: 72 percent / DMSO, oxalyl chloride, NEt3 / 1) CH2Cl2, -78 deg C, 1 h, 2) 0 deg C, 1 h 8: 75 percent / aq. HCl / methanol / 96 h / Ambient temperature View Scheme

<b>Multi-step reaction with 3 steps<br /> </b>1: 98 percent / D-Camphor-10-sulfonic acid / benzene / 12 h / Heating<br />2: 84 percent / LiAlH₄ / tetrahydrofuran / 0.25 h / 0 &deg;C<br />3: 98 percent / D-camphor-10-sulfonic acid / CH₂Cl₂ / 1 h / Ambient temperature<br /> <br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1: 80 percent / LiAlH₄ / tetrahydrofuran / 0.5 h / 0 &deg;C<br />2: 98 percent / D-camphor-10-sulfonic acid / CH₂Cl₂ / 1 h / Ambient temperature<br /> <br /> &nbsp;

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '2216194', constants.ctx, '0')">camphor-10-sulfonic acid</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1730800', constants.ctx, '0')">dichloromethane</a> <br />1&nbsp;h;&nbsp;&nbsp;Ambient temperature;&nbsp;<br /> &nbsp;