1: DIAD; Ph3P / tetrahydrofuran / 0 - 20 °C 2: NaIO4; OsO4 / methanol; H2O / 3 h / 0 - 20 °C 3: 2.09 g / NaBH4 / methanol / 1 h / 0 °C 4: 91 percent / NH3 / methanol / 24 h / 100 °C 5: 95 percent / aq. HCl / methanol / 3 h / 20 °C View Scheme

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '11460447', constants.ctx, '0')">lithium aluminium tetrahydride</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '102391', constants.ctx, '0')">tetrahydrofuran</a> <br />T=20&deg;C;&nbsp;3&nbsp;h;&nbsp;<br /> &nbsp;

<b>Multi-step reaction with 6 steps<br /> </b>1.1: Ph₃P; I₂; imidazole<br />1.2: Zn / methanol<br />2.1: 80 percent / CH₂Cl₂; tetrahydrofuran / 3 h / -40 - 0 &deg;C<br />3.1: Grubbs catalyst / CH₂Cl₂ <br />4.1: PCC / CH₂Cl₂ <br />5.1: 80 percent / CuBr*Me₂S; TMSCl; HMPA / tetrahydrofuran / -78 - 0 &deg;C<br />6.1: 98 percent / LiAlH₄ / tetrahydrofuran / 3 h / 20 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 4 steps<br /> </b>1: Grubbs catalyst / CH₂Cl₂ <br />2: PCC / CH₂Cl₂ <br />3: 80 percent / CuBr*Me₂S; TMSCl; HMPA / tetrahydrofuran / -78 - 0 &deg;C<br />4: 98 percent / LiAlH₄ / tetrahydrofuran / 3 h / 20 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1: PCC / CH₂Cl₂ <br />2: 80 percent / CuBr*Me₂S; TMSCl; HMPA / tetrahydrofuran / -78 - 0 &deg;C<br />3: 98 percent / LiAlH₄ / tetrahydrofuran / 3 h / 20 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1: 80 percent / CuBr*Me₂S; TMSCl; HMPA / tetrahydrofuran / -78 - 0 &deg;C<br />2: 98 percent / LiAlH₄ / tetrahydrofuran / 3 h / 20 &deg;C<br /> <br /> &nbsp;