Methanol → 1-{2-[(7-Hydroxyheptanoyl)(methyl)amino]ethyl}piperidin-4-yl biphenyl-2-ylcarbamate

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Reaction Steps

Lithium borohydride (39 mg, 1.80 mmol) was suspended in tetrahydrofuran (6 mL), methanol (73 μL, 1.80 mmol) and a solution of the compound (235 mg, 0.450 mmol) obtained in Example 39a in tetrahydrofuran (7 mL) was added, and the mixture was stirred at room temperature for 2 days. A 1 N aqueous sodium hydroxide solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate (×3). The organic layer was washed with saturated sodium chloride solution and dried with anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the resulting residue was purified by NH silica gel column chromatography (ethyl acetate:methanol=50:1, v/v) to give the title compound (163 mg; yield, 75%) as a white solid.

Provenance & Evidence