ruthenium trichloride; sodium periodate in tetrachloromethane; water; acetonitrile 2 h;

1: NaIO4, RuCl3*H2O / acetonitrile; CCl4; H2O / 2 h 2: 1.) 3N HCl, 2.) Dowex 50*8 / 1.) THF, room temperature, 2 h. View Scheme

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '3587189', constants.ctx, '0')">hydrogen</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '11342936', constants.ctx, '0')">palladium dihydroxide</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1098229', constants.ctx, '0')">methanol</a> <br />P=760&nbsp;Torr;&nbsp;72&nbsp;h;&nbsp;&nbsp;Ambient temperature;&nbsp;<br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1: 1.) H₂ / 1.) Pd(OH)2/C / 1.) MeOH, 70 psi, 3 d, 2.) 1,4-dioxane, room temp., 16 h<br />2: 96 percent / p-toluensulfonic acid monohydrate / methanol / 4 h / Heating<br /> <br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1: 1.) Et₂AlCl / 1.) Et₂O, room temp., 15 min, 2.) Et₂O, -60 deg C, 6 h<br />2: 1.) H₂ / 1.) Pd(OH)2/C / 1.) MeOH, 70 psi, 3 d, 2.) 1,4-dioxane, room temp., 16 h<br />3: 96 percent / p-toluensulfonic acid monohydrate / methanol / 4 h / Heating<br /> <br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1.1: 25 mg / Na₂CO₃ / CH₂Cl₂; H₂O / 16 h / 22 &deg;C<br />2.1: ozone / diethyl ether; CH₂Cl₂ / 0.08 h / -78 &deg;C<br />2.2: 28 percent / LiBH₄ / diethyl ether; CH₂Cl₂ / -78 - 22 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1.1: PI(OAc)2 / methanol; CH₂Cl₂ / 1 h / 0 &deg;C<br />1.2: 76 percent / aq. HCl / methanol; CH₂Cl₂ / 0 - 20 &deg;C<br />2.1: 25 mg / Na₂CO₃ / CH₂Cl₂; H₂O / 16 h / 22 &deg;C<br />3.1: ozone / diethyl ether; CH₂Cl₂ / 0.08 h / -78 &deg;C<br />3.2: 28 percent / LiBH₄ / diethyl ether; CH₂Cl₂ / -78 - 22 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 4 steps<br /> </b>1.1: 82 percent / AgOAc; N-[2-PPh₂-benzylidene]-L-tert-leucine (4-methoxyphenyl)amide / tetrahydrofuran; propan-2-ol / 18 h / -78 &deg;C<br />2.1: PI(OAc)2 / methanol; CH₂Cl₂ / 1 h / 0 &deg;C<br />2.2: 76 percent / aq. HCl / methanol; CH₂Cl₂ / 0 - 20 &deg;C<br />3.1: 25 mg / Na₂CO₃ / CH₂Cl₂; H₂O / 16 h / 22 &deg;C<br />4.1: ozone / diethyl ether; CH₂Cl₂ / 0.08 h / -78 &deg;C<br />4.2: 28 percent / LiBH₄ / diethyl ether; CH₂Cl₂ / -78 - 22 &deg;C<br /> <br /> &nbsp;