1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 20 °C 2: RuCl2(tricyclohexylphosphine)2(benzylidene) / dichloromethane / 12 h / |Inert atmosphere; |Reflux 3: formic acid; hydrogen; palladium 10 on activated carbon / methanol / 14 h / 20 °C View Scheme

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '110354', constants.ctx, '0')">4-(N,N-dimethlyamino)pyridine</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '605283', constants.ctx, '0')">triethylamine</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1730800', constants.ctx, '0')">dichloromethane</a> <br />T=20&deg;C;&nbsp;12&nbsp;h;&nbsp;<br /> &nbsp;

Stage #1: <a href="#" onclick="return RXDsubstances(event, this, '143124', constants.ctx, '0')">1,3-Dihydro-1,3-dioxo-2-(2-propenyl)-2H-isoindole</a> <b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '4151240', constants.ctx, '0')">lithium triethylborohydride</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '102391', constants.ctx, '0')">tetrahydrofuran</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '1730800', constants.ctx, '0')">dichloromethane</a> <br />T=-78&deg;C;&nbsp;<br />Stage #2: <a href="#" onclick="return RXDsubstances(event, this, '385737', constants.ctx, '0')">acetic anhydride</a> &nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '102391', constants.ctx, '0')">tetrahydrofuran</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '1730800', constants.ctx, '0')">dichloromethane</a> <br />T=-78 - 20&deg;C;&nbsp;<br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1: NaBH₄ / methanol / -5 - 0 &deg;C<br />2: 84 percent / Et₃N; DMAP / CH₂Cl₂ / 12 h / 20 &deg;C<br /> <br /> &nbsp;