Sodium borohydride → HCID 68409208, compound

Participants

Reaction Steps

The free base of {5-[(methylamino)methyl]-3-phenyl-2-thienyl}(phenyl)methanone (274 mg) obtained in Example 13 was dissolved in tetrahydrofuran (3 mL) and methanol (2 mL), and sodium borohydride (51 mg) was added at room temperature. After stirring for 3 hr, the solvent was evaporated under reduced pressure, water was added to the residue, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (eluent:hexane-ethyl acetate=1:1→1:9) to give a free base of the title compound (106 mg) as a pale-yellow oil. To a solution of fumaric acid (40 mg) in ethanol (3 mL) was added a solution of the obtained free base in ethyl acetate (4 mL), and the solvent was evaporated under reduced pressure. The residue was crystallized from a mixed solvent of ethyl acetate and 2-propanol and recrystallized from ethanol to give the title compound as colorless crystals (yield 40 mg, yield 32%).

Provenance & Evidence