1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 25 - 30 °C 1.2: 1 h / 0 - 5 °C 2.1: sodium methylate / methanol; N,N-dimethyl-formamide / 0 - 5 °C 3.1: ethyl acetate / 25 - 30 °C 4.1: sulfuric acid; water / 5 - 10 °C View Scheme

1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 25 - 30 °C 1.2: 1 h / 0 - 5 °C 2.1: sodium methylate / methanol; N,N-dimethyl-formamide / 0 - 5 °C 3.1: ethyl acetate / 25 - 30 °C 4.1: sulfuric acid; water / 5 - 10 °C 5.1: ethyl acetate / 25 - 30 °C 6.1: acetic acid / dichloromethane; water / 25 - 30 °C 6.2: 25 - 30 °C View Scheme

1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 25 - 30 °C 1.2: 1 h / 0 - 5 °C 2.1: sodium methylate / methanol; N,N-dimethyl-formamide / 0 - 5 °C 3.1: ethyl acetate / 25 - 30 °C 4.1: sodium methylate / methanol; N,N-dimethyl-formamide / 26 h / 25 - 45 °C 5.1: sulfuric acid; water / 2.5 h / 0 - 10 °C / Inert atmosphere View Scheme

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1098214', constants.ctx, '0')">hydrogenchloride</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '3587155', constants.ctx, '0')">water</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '506104', constants.ctx, '0')">ethyl acetate</a> <br />T=25 - 30&deg;C;&nbsp;<br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1: toluene-4-sulfonic acid / dichloromethane / 25 - 30 &deg;C<br />2: water; sodium hydroxide / tetrahydrofuran; methanol / 25 - 30 &deg;C<br />3: hydrogenchloride / water; ethyl acetate / 25 - 30 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 5 steps<br /> </b>1: cerium(III) chloride / tetrahydrofuran / 0 - 5 &deg;C<br />2: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 0 - 5 &deg;C<br />3: toluene-4-sulfonic acid / dichloromethane / 25 - 30 &deg;C<br />4: water; sodium hydroxide / tetrahydrofuran; methanol / 25 - 30 &deg;C<br />5: hydrogenchloride / water; ethyl acetate / 25 - 30 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 4 steps<br /> </b>1: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 0 - 5 &deg;C<br />2: toluene-4-sulfonic acid / dichloromethane / 25 - 30 &deg;C<br />3: water; sodium hydroxide / tetrahydrofuran; methanol / 25 - 30 &deg;C<br />4: hydrogenchloride / water; ethyl acetate / 25 - 30 &deg;C<br /> <br /> &nbsp;