1: 90 percent / Et3N; DMAP / CH2Cl2 / 0 °C 2: 62 percent / NaH; Pd(PPh3)4 / dimethylsulfoxide; tetrahydrofuran / 45 °C 3: aq. NaOH View Scheme

4-(N,N-dimethlyamino)pyridine; triethylamine in dichloromethane

1: DMAP / pyridine 2: 85 percent / Pd(PPh3)4 / dimethylformamide / 55 °C 3: OsO4, trimethylamine oxide 4: NH3 View Scheme

1: DMAP / pyridine 2: 43 percent / Pd(PPh3)4 / dimethylformamide / 55 °C 3: NaOH / tetrahydrofuran; H2O 4: OsO4, trimethylamine N-oxide 5: NH3 View Scheme

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '11536633', constants.ctx, '0')">lithium borohydride</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, '1098229', constants.ctx, '0')">methanol</a> <br /> <br /> &nbsp;

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '11536633', constants.ctx, '0')">lithium borohydride</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, '1098229', constants.ctx, '0')">methanol</a> <br /> <br /> &nbsp;

<b>Multi-step reaction with 5 steps<br /> </b>1: 94 percent / Pd, trans-1,2-(o-PPh₂-C₆H₄-C(O)NH)2-cyclo-C₆H₁₀ / Ambient temperature<br />2: 94 percent / SnCl₂*2H₂O / acetonitrile / Ambient temperature<br />3: 91 percent / K₂CO₃ / 50 &deg;C<br />4: 84 percent / Mo(CO)6, boric acid, methanol<br />5: 95 percent / LAH / diethyl ether / Ambient temperature<br /> <br /> &nbsp;

<b>Multi-step reaction with 5 steps<br /> </b>1: (dba)3Pd₂*CHCl₃, Ph₃P (TPP) / tetrahydrofuran / Ambient temperature<br />2: 94 percent / SnCl₂*2H₂O / acetonitrile / Ambient temperature<br />3: 91 percent / K₂CO₃ / 50 &deg;C<br />4: 84 percent / Mo(CO)6, boric acid, methanol<br />5: 95 percent / LAH / diethyl ether / Ambient temperature<br /> <br /> &nbsp;