1.1: nitric acid; trifluoroacetic acid; trifluoroacetic anhydride / CH2Cl2 / -35 - -30 °C 2.1: NaOH; methanol / 23 °C 3.1: acetic acid; perchloric acid; hydrogen / Pd/C / 15.5 h / 2172.08 - 2585.81 Torr 3.2: NaHCO3 / H2O; CH2Cl2 / 23 °C / pH 8.0 View Scheme

<b>Multi-step reaction with 2 steps<br /> </b>1: Red-Al; sodium bis(2-methoxyethoxy)aluminum hydride / toluene; tetrahydrofuran / -10 - 0 &deg;C<br />2: pyridine / CH₂Cl₂ / -5 - 0 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1.1: aluminum chloride / CH₂Cl₂ / 22 - 28 &deg;C<br />1.2: aq. HCl / CH₂Cl₂ / -5 - 1 &deg;C<br />2.1: Red-Al; sodium bis(2-methoxyethoxy)aluminum hydride / toluene; tetrahydrofuran / -10 - 0 &deg;C<br />3.1: pyridine / CH₂Cl₂ / -5 - 0 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 5 steps<br /> </b>1.1: aq. sodium hydroxide; sodium carbonate / 0 - 23 &deg;C<br />2.1: phosphorus pentachloride / CH₂Cl₂ / -10 - 20 &deg;C<br />3.1: aluminum chloride / CH₂Cl₂ / 22 - 28 &deg;C<br />3.2: aq. HCl / CH₂Cl₂ / -5 - 1 &deg;C<br />4.1: Red-Al; sodium bis(2-methoxyethoxy)aluminum hydride / toluene; tetrahydrofuran / -10 - 0 &deg;C<br />5.1: pyridine / CH₂Cl₂ / -5 - 0 &deg;C<br /> <br /> &nbsp;