1: n-BuLi / diethyl ether; tetrahydrofuran; hexane / 1.) -70 deg C, 20 min, 2.) -70 deg C, 2 h; -50 deg C, 30 min 2: KH / tetrahydrofuran / 1.) r.t., 20 min, 2.) r.t., 20 min 3: toluene / 2 h / Heating 4: H2 / PtO2 / ethyl acetate / 1 h / 2068.6 Torr 5: HCl / ethyl acetate / 1 h / 0 °C 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;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1098229', constants.ctx, '0')">methanol</a> <br />1&nbsp;h;&nbsp;<br /> &nbsp;

<b>Multi-step reaction with 8 steps<br /> </b>1: 80percent m-CPBA / CH₂Cl₂ / 4 h / Ambient temperature<br />2: 78 percent / aq. K₂CO₃ / methanol / 72 h / Ambient temperature<br />3: 48 percent / 1-methyl-2-pyrrolidinone / 16 h / 180 &deg;C<br />4: 5 N HCl, H₂ / Pd(OH)2/C / ethanol / 6 h / 40 &deg;C / 2068.6 Torr<br />5: 1 N NaOH / dioxane / 18 h / Ambient temperature<br />6: 43 percent / DMAP / CH₂Cl₂ / 18 h / Ambient temperature<br />7: 97 percent / KOH / ethanol / 2 h / Ambient temperature<br />8: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -70 deg C, 20 min<br /> <br /> &nbsp;