Diisobutylaluminum hydride → (3-{3-[(2-Chloro-3-trifluoromethyl-benzyl)-diphenylethyl-amino]-propoxy}-phenyl)-acetaldehyde

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Reaction Conditions

Reaction Steps

A solution of (3-{3-[(2-chloro-3-trifluoromethyl-benzyl)-diphenylethyl-amino]-propoxy}-phenyl)-acetic acid methyl ester (350 mg, 1.68 mmole) in anhydrous toluene (20 ml) was cooled down to −40° C. in a dry ice/acetonitrile bath. DIBAL-H (1.25 ml, 1.5M solution in toluene, Aldrich) was added in a dropwise fashion. The resulting mixture was stirred at −40° C. for 3 hours and then quenched with 0.01N HCl (aq.). The crude material was concentrated in vacuo and then extracted with EtOAc (3×). The combined organic layers were washed with brine (1×), dried over sodium sulfate, filtered and concentrated in vacuo. Preparative HPLC (YMC, 75×30 mm, 25 ml/min, 70-100% CH3CN) afforded the title compound as an oil, 0.15 g (45%). MS(ES) m/e 566.2 (M+).

Provenance & Evidence