1: NaBH4 3: 1.) Na2CO3, 2.) aq. HCl / 1.) methyl isobutyl ketone 4: 1.) aq. Na2CO3, 2.) NaOH View Scheme

1: NaBH4 3: 1.) Na2CO3, 2.) aq. HCl / 1.) methyl isobutyl ketone 4: 1.) aq. Na2CO3, 2.) NaOH 6: H2 / Pd/C View Scheme

1: NaBH4 3: 1.) Na2CO3, 2.) aq. HCl / 1.) methyl isobutyl ketone 4: 1.) aq. Na2CO3, 2.) NaOH View Scheme

<b>Multi-step reaction with 4 steps<br /> </b>1: H₂ / 10percent Pd/C / ethyl acetate / 20 &deg;C / 1 Torr<br />2: 70 percent / Et₃N / CH₂Cl₂ / 1.5 h / -20 &deg;C<br />3: 80 percent / RuCl₃*6H₂O, NaIO₄ / H₂O; acetonitrile; CCl₄ / 2.5 h / 20 &deg;C<br />4: diethyl ether; methanol / 0.17 h<br /> <br /> &nbsp;

<b>Multi-step reaction with 7 steps<br /> </b>1: 1) CuCN / 1) THF, -70 deg C, 1 h, 2) THF, a) -65 deg C,, 1 h, b) -30 deg C, 2.5 h<br />3: CF₃COOH, H₂O / 3 h / 0 - 20 &deg;C<br />4: H₂ / 10percent Pd/C / ethyl acetate / 20 &deg;C / 1 Torr<br />5: 70 percent / Et₃N / CH₂Cl₂ / 1.5 h / -20 &deg;C<br />6: 80 percent / RuCl₃*6H₂O, NaIO₄ / H₂O; acetonitrile; CCl₄ / 2.5 h / 20 &deg;C<br />7: diethyl ether; methanol / 0.17 h<br /> <br /> &nbsp;

<b>Multi-step reaction with 4 steps<br /> </b>1.1: tBuOK / 2-methyl-propan-2-ol; tetrahydrofuran / 0.25 h / 0 &deg;C<br />1.2: 91 percent / tetrahydrofuran; 2-methyl-propan-2-ol / 15 h / 20 &deg;C<br />2.1: 74 percent / MeSO₂Cl; iPr₂NEt / CH₂Cl₂ / 5 h / -78 - 20 &deg;C<br />3.1: Ph₃COOK / tetrahydrofuran; toluene / -78 - -20 &deg;C<br />4.1: 84 percent / DMDO / acetone / 3 h / 0 - 20 &deg;C<br /> <br /> &nbsp;