3,4,5-Trimethoxybenzaldehyde → HCID 59913943, compound

Participants

Reaction Steps

(S)-2-Amino-1-{4-[bis-(4-fluoro-phenyl)-methyl]-piperazin-1-yl}-4-methyl-pentan-1-one (0.500 g, 1.25 mmol, Example 53) and 3,4,5-trimethoxybenzaldehyde (0.244 g, 1.25 mmol, Aldrich, Milwaukee, Wis.) were mixed in CH2Cl2 (6 mL). After stirring at ambient temperature under nitrogen atmosphere for 30 minutes, the solution was cooled to 0° C. in an ice-water bath. To this solution was added sodium triacetoxyborohydride (0.396 g, 1.87 mmol). The resulting reaction mixture was stirred for, in succession, 30 minutes at 0° C. and 12 hours at ambient temperature. Twenty milliliters of saturated aqueous NaHCO3 solution was added to the reaction mixture and the resulting mixture was stirred for 15 minutes. The two layers were separated, and the aqueous layer was extracted with CH2Cl2 (2×20 mL). The combined organic solution was dried over Na2SO4. TLC (50% EtOAc in Hexanes as the eluant) showed two spots with Rf values 0.46 and 0.15. The solution was concentrated in vacuo affording a viscous oil. The lower spot on TLC (Rf=0.15) was isolated by flash chromatography (50% EtOAc in hexanes). Eighty-four percent (0.61 g) of the pure titled compound was obtained as a white foam: mp 58-62° C. APCI-MS m/z 582.4 (MH+).

Provenance & Evidence