5 palladium on charcoal; hydrogen in methanol 24 h;

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1911434', constants.ctx, '0')">di-tert-butylazodicarboxylate</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '605283', constants.ctx, '0')">triethylamine</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '610776', constants.ctx, '0')">triphenylphosphine</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '635760', constants.ctx, '0')">toluene</a> <br />T=20&deg;C;&nbsp;18&nbsp;h;&nbsp;&nbsp;Cooling with ice;&nbsp;<br /> <br /> &nbsp;

<b>Multi-step reaction with 5 steps<br /> </b>1.1: sodium tetrahydroborate; methanol / 3 h / 20 &deg;C / Cooling with ice<br />1.2: 16 h / 20 &deg;C<br />2.1: potassium carbonate; N-benzyl-N,N,N-triethylammonium chloride / 1,4-dioxane / 4 h / 90 &deg;C<br />3.1: sodium hydride / dichloromethane / 0.17 h / 0 &deg;C / Inert atmosphere<br />3.2: 17 h / 20 &deg;C / Cooling with ice<br />4.1: hydrogen bromide; acetic acid; phenol / 12 h / 75 &deg;C / sealed tube; microwave irradiation<br />5.1: dmap / dichloromethane / 1 h<br /> <br /> &nbsp;