1: 1.) lithium bis(trimethylsilyl)amide / 1.) THF, -80 deg C, 30 min, 2.) THF, -80 deg C, 20 min 2: 81 percent / LiAlH4 / diethyl ether / 2 h / Ambient temperature 3: 83 percent / imidazole / dimethylformamide / 14 h / Ambient temperature 4: 54 percent / triphenylphosphine, diethyl azodicarboxylate / benzene / 12 h / Heating 5: 86 percent / LiAlH4 / diethyl ether / 1 h / Ambient temperature 6: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature 7: 80 percent / pyridine / 14 h / Ambient temperature 8: 1.) H2, 2.) Et3N / 1.) Pd(OH)2 / 1.) MeOH, 1 atm, 1 h, 2.) reflux, 1.5 h 9: 71 percent / a) conc. HCl, b) Dowex 1-X8, OH(1-)-form / a) MeOH, reflux, 30 min, b) H2O View Scheme

<b>Multi-step reaction with 5 steps<br /> </b>1: 1.) triethylaluminum / 1.) CH₂Cl₂, hexane, 30 min, 2.) CH₂Cl₂, r.t., 14 h<br />2: 88 percent / Et₃N / CH₂Cl₂ / 0.5 h / 0 &deg;C<br />3: 85 percent / N,N-diisopropylethylamine / CHCl₃ / 1 h / Heating<br />4: 91 percent / LiAlH₄ / diethyl ether / 2 h / Ambient temperature<br />5: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -80 deg C, 2 h, 2.) -80 deg C to r.t.<br /> <br /> &nbsp;

<b>Multi-step reaction with 4 steps<br /> </b>1: 88 percent / Et₃N / CH₂Cl₂ / 0.5 h / 0 &deg;C<br />2: 85 percent / N,N-diisopropylethylamine / CHCl₃ / 1 h / Heating<br />3: 91 percent / LiAlH₄ / diethyl ether / 2 h / Ambient temperature<br />4: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -80 deg C, 2 h, 2.) -80 deg C to r.t.<br /> <br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1: 85 percent / N,N-diisopropylethylamine / CHCl₃ / 1 h / Heating<br />2: 91 percent / LiAlH₄ / diethyl ether / 2 h / Ambient temperature<br />3: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -80 deg C, 2 h, 2.) -80 deg C to r.t.<br /> <br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1: 91 percent / LiAlH₄ / diethyl ether / 2 h / Ambient temperature<br />2: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -80 deg C, 2 h, 2.) -80 deg C to r.t.<br /> <br /> &nbsp;

<b>Multi-step reaction with 5 steps<br /> </b>1: 1.) triethylaluminum / 1.) CH₂Cl₂, hexane, 30 min, 2.) CH₂Cl₂, r.t., 14 h<br />2: 88 percent / Et₃N / CH₂Cl₂ / 0.5 h / 0 &deg;C<br />3: 85 percent / N,N-diisopropylethylamine / CHCl₃ / 1 h / Heating<br />4: 91 percent / LiAlH₄ / diethyl ether / 2 h / Ambient temperature<br />5: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -80 deg C, 2 h, 2.) -80 deg C to r.t.<br /> <br /> &nbsp;