Synthesis of optically active CCG-1423 <i>S</i>.

<p>Reagents and conditions: (a) benzyl alcohol, iron(III) acetylacetonate, Na₂CO₃, heptane, reflux (–H₂O), 12 h, 87%; (b) <i>N</i>-hydroxyphthalimide, dimethyl azodicarboxylate, PPh₃, THF, RT, 1 h, 63%; (c) H₂, Pd-C, MeOH, RT, 2 h, 94%; (d) (COCl)₂, <i>N</i>,<i>N</i>-dimethylformamide, CH₂Cl₂, RT, 1 h; (e) 4-chloroaniline, CH₂Cl₂, 0°C, 2 h, 66% (2 steps); (f) NH₂NH₂-H₂O, MeOH, RT, 5 min, 52%; (g) 3,5-bis(trifluoromethyl)benzoic acid, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, 4-dimethylaminopyridine, CH₂Cl₂, RT, 1 h, 79%.