1: 93 percent / DCC, HOBt, Et3N / tetrahydrofuran / 5 h / Ambient temperature 2: 88 percent / TBAF / tetrahydrofuran / 0.5 h / 0 °C 3: 77 percent / MsCl, Et3N / CH2Cl2 / 16 h / Ambient temperature 4: 75 percent / MnO2 / CHCl3 / 6 h / Heating 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 />&nbsp;Yield given;&nbsp;<br /> &nbsp;

<b>Multi-step reaction with 5 steps<br /> </b>1: OsO₄, NMO / acetonitrile; H₂O / 12 h / Ambient temperature<br />2: 84 percent / imidazole / dimethylformamide / 4 h / 0 &deg;C<br />3: 95 percent / pyridine / 1 h / 0 &deg;C<br />4: 93 percent / NaN₃ / dimethylformamide / 4 h / Ambient temperature<br />5: H₂ / Pd-C / methanol<br /> <br /> &nbsp;

<b>Multi-step reaction with 4 steps<br /> </b>1: 84 percent / imidazole / dimethylformamide / 4 h / 0 &deg;C<br />2: 95 percent / pyridine / 1 h / 0 &deg;C<br />3: 93 percent / NaN₃ / dimethylformamide / 4 h / Ambient temperature<br />4: H₂ / Pd-C / methanol<br /> <br /> &nbsp;

<b>Multi-step reaction with 11 steps<br /> </b>1: 72 percent / NaH, n-BuLi / tetrahydrofuran / 1 h / 0 &deg;C<br />2: 1.) NaH, LDA; 2.) DBU / 1.) THF, -78 deg C, 1 h; 2.) benzene, 60 deg C, 3 h<br />3: 61 percent / CH₂Cl₂ / 4 h / Ambient temperature<br />4: H₂ / Pd/C / methanol / 3 h / 50 &deg;C<br />5: pyridine; CH₂Cl₂ / 2 h / Ambient temperature<br />6: K₂CO₃ / methanol / 0.5 h / Ambient temperature<br />7: OsO₄, NMO / acetonitrile; H₂O / 12 h / Ambient temperature<br />8: 84 percent / imidazole / dimethylformamide / 4 h / 0 &deg;C<br />9: 95 percent / pyridine / 1 h / 0 &deg;C<br />10: 93 percent / NaN₃ / dimethylformamide / 4 h / Ambient temperature<br />11: H₂ / Pd-C / methanol<br /> <br /> &nbsp;