1: NaOMe / tetrahydrofuran; methanol / 19 h / Ambient temperature 2: NH2NH2 / 20 percent Pd(OH)2/C / methanol / 19 h / Heating 3: H2 / 20 percent Pd(OH)2/C / acetic acid; H2O / 22 h / 760 Torr / Ambient temperature View Scheme

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '113917', constants.ctx, '0')">N-iodo-succinimide</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '19253605', constants.ctx, '0')">4 A molecular sieve</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '3598402', constants.ctx, '0')">silver trifluoromethanesulfonate</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1730800', constants.ctx, '0')">dichloromethane</a> <br />T=0&deg;C;&nbsp;2&nbsp;h;&nbsp;<br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1: 57 percent / NaH / dimethylformamide / 4.5 h / 0 - 20 &deg;C<br />2: TfOH, NIS / diethyl ether; CH₂Cl₂ / 0.5 h / -15 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1: 90 percent / NaN₃ / dimethylformamide / 5 h / 80 &deg;C<br />2: 57 percent / NaH / dimethylformamide / 4.5 h / 0 - 20 &deg;C<br />3: TfOH, NIS / diethyl ether; CH₂Cl₂ / 0.5 h / -15 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1: 60 percent / Novozym 435 / toluene; various solvent(s) / pH 6.2<br />2: 65 percent / 4 Angstroem molecular sieves; N-iodosuccinimide; AgOTf / CH₂Cl₂ / 2 h / 0 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 4 steps<br /> </b>1: TfN₃, Et₃N, CuSO₄ / CH₂Cl₂; methanol / 21 h / Ambient temperature<br />2: pyridine, DMAP / 23 h / Ambient temperature<br />3: 71 percent / Novozym 435 (Candida antarctica lipase), sodium phosphate buffer (pH 6.2) / toluene / 72 h / Ambient temperature<br />4: TfOH, NIS / diethyl ether; CH₂Cl₂ / 0.5 h / -15 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1: 57 percent / NaH / dimethylformamide / 4.5 h / 0 - 20 &deg;C<br />2: TfOH, NIS / diethyl ether; CH₂Cl₂ / 0.5 h / -15 &deg;C<br /> <br /> &nbsp;