hydrogen; palladium dihydroxide in ethanol

hydrogen; palladium dihydroxide in ethanol; dichloromethane Hydrogenolysis;

<b>Multi-step reaction with 5 steps<br /> </b>1: 80percent AcOH / 4 h / 90 &deg;C<br />2: pyridine / 72 h / Ambient temperature<br />3: 1.) N,O-bis(trimethylsilyl)acetamide, 2.) TMS-triflate / 1.) CH₃CN, reflux, 1 h, 2.) 65 deg C, 2 h<br />4: 97 percent / NaOMe / methanol / 0.17 h / Ambient temperature<br />5: 1.) pTsCl, 2.) NaH / 1.) Py, room temperature, 20 h, 2.) DMF, 0 deg C, 72 h<br /> <br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1: 97 percent / NaOMe / methanol / 0.17 h / Ambient temperature<br />2: 1.) pTsCl, 2.) NaH / 1.) Py, room temperature, 20 h, 2.) DMF, 0 deg C, 72 h<br /> <br /> &nbsp;

<b>Multi-step reaction with 7 steps<br /> </b>1: 1.) NaH / 1.) DMF, -5 deg C, 1.5 h, 2.) room temperature, 3 h<br />2: 90 percent / pyridine / 3 h / Ambient temperature<br />3: 80percent AcOH / 4 h / 90 &deg;C<br />4: pyridine / 72 h / Ambient temperature<br />5: 1.) N,O-bis(trimethylsilyl)acetamide, 2.) TMS-triflate / 1.) CH₃CN, reflux, 1 h, 2.) 65 deg C, 2 h<br />6: 97 percent / NaOMe / methanol / 0.17 h / Ambient temperature<br />7: 1.) pTsCl, 2.) NaH / 1.) Py, room temperature, 20 h, 2.) DMF, 0 deg C, 72 h<br /> <br /> &nbsp;