1: 90 percent / CBr4, PPh3 / CH2Cl2 / 4 h / 25 °C 2: 4.2 g / BuLi / hexane; tetrahydrofuran; hexamethylphosphoric acid triamide 3: 75 percent / TsOH / methanol / 2 h / Heating 4: 76 percent / Jones reagent / acetone / 0 °C 5: CF3COOH / 24 h / 20 °C View Scheme

1: 90 percent / CBr4, PPh3 / CH2Cl2 / 4 h / 25 °C 2: 4.2 g / BuLi / hexane; tetrahydrofuran; hexamethylphosphoric acid triamide 3: 75 percent / TsOH / methanol / 2 h / Heating 4: 76 percent / Jones reagent / acetone / 0 °C 5: 1.) CF3COOH, 2.) H2, Ni(OAc)2, NaBH4, ethylenediamine / 2.) Ni / 1.) 20 deg C, 24 h, 2.) ethanol, 20 deg C View Scheme

1: 90 percent / CBr4, PPh3 / CH2Cl2 / 4 h / 25 °C 2: 4.2 g / BuLi / hexane; tetrahydrofuran; hexamethylphosphoric acid triamide 3: 75 percent / TsOH / methanol / 2 h / Heating 4: 76 percent / Jones reagent / acetone / 0 °C 5: 1.) CF3COOH, 2.) H2, Ni(OAc)2, NaBH4, ethylenediamine / 2.) Ni / 1.) 20 deg C, 24 h, 2.) ethanol, 20 deg C 6: 1.) Ph3P, 2,2'-dipyridyl disulfide, 2.) AgClO4 / 1.) MeCN, 2.) toluene, reflux 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;<a href="#" onclick="return RXDsubstances(event, this, '19241793', constants.ctx, '0')">Ru-carbon</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1718733', constants.ctx, '0')">ethanol</a> <br />T=20&deg;C;&nbsp;<br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1: 88 percent / Cu₂Cl₂, aq. tert-butylamine, NH₂OH*HCl / methanol / 2 h / 40 &deg;C<br />2: 94 percent / H₂ / 1.) Ru/C, 2.) Pd/C / ethanol / 20 &deg;C<br /> <br /> &nbsp;