<b>Multi-step reaction with 4 steps<br /> </b>1: 70 percent / potassium 3-aminopropylamide / hexane / 5 h / 20 &deg;C<br />2: 76 percent / sulfur trioxide pyridine complex; triethylamine / CH₂Cl₂; dimethylsulfoxide / 20 &deg;C<br />3: hexane / -20 - 0 &deg;C<br />4: diethylzinc; (1S)-(+)-3-exo-(dimethylamino)isoborneol / hexane / 0 &deg;C<br /> <br /> &nbsp;

Stage #1: <a href="#" onclick="return RXDsubstances(event, this, '3535841', constants.ctx, '0')">vinyl-magnesium bromide</a> <b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '11405916', constants.ctx, '0')">copper(l) iodide</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '102391', constants.ctx, '0')">tetrahydrofuran</a> <br />T=-40&deg;C;&nbsp;0.25&nbsp;h;&nbsp;&nbsp;Inert atmosphere;&nbsp;<br />Stage #2: <b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1099903', constants.ctx, '0')">N,N,N',N',N'',N''-hexamethylphosphoric triamide</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '956578', constants.ctx, '0')">triethyl phosphite</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '102391', constants.ctx, '0')">tetrahydrofuran</a> <br />T=-40&deg;C;&nbsp;0.0833333&nbsp;h;&nbsp;&nbsp;Inert atmosphere;&nbsp;<br />Stage #3: <a href="#" onclick="return RXDsubstances(event, this, '4951264', constants.ctx, '0')">11-bromo-1-hydroxyundecane</a> &nbsp;Further stages;&nbsp;<br /> &nbsp;

<b>Multi-step reaction with 5 steps<br /> </b>1.1: n-butyllithium / tetrahydrofuran; hexane; hexamethylphosphoric acid triamide / 0 - 20 &deg;C<br />1.2: 85 percent / 4-toluenesulfonic acid monohydrate / methanol / 20 &deg;C<br />2.1: 70 percent / potassium 3-aminopropylamide / hexane / 5 h / 20 &deg;C<br />3.1: 76 percent / sulfur trioxide pyridine complex; triethylamine / CH₂Cl₂; dimethylsulfoxide / 20 &deg;C<br />4.1: hexane / -20 - 0 &deg;C<br />5.1: diethylzinc; (1S)-(+)-3-exo-(dimethylamino)isoborneol / hexane / 0 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 4 steps<br /> </b>1: 1) nBuLi / 1) -78 to -20 deg C, 2) HMPA, RT<br />2: MeOH, H₂O, p-TsOH<br />3: 87 percent / NaH, 1,3-diaminopropane / cyclopentane<br />4: hydrogenation<br /> <br /> &nbsp;