3,5-Bis(trifluoromethyl)benzaldehyde → N-(5-((1R,2S)-2-(3,5-Bis(trifluoromethyl)benzylamino)-1-hydroxypropyl)-2-hydroxyphenyl)methanesulfonamide

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Reaction Steps

Borane-pyridine complex (130 μL, 1.24 mmol) was added to a methanol solution (4 mL) of an amine (3) (107 mg, 0.41 mmol), 3,5-bis(trifluoromethyl)benzaldehyde (90 μL, 0.54 mmol) at 40° C. and the mixture was stirred for 1.5 hours. The reaction mixture was allowed to cool to room temperature and extracted after addition of water with a mixed solvent (ethyl acetate: methanol=10:1), and the organic layer was washed with saturated aqueous sodium chloride solution. The organic layer was dried and concentrated, and the crude product obtained was purified by amine silica gel column chromatography (eluant:chloroform:methanol=7:1), to give a desired amine (5) as a white solid (132 mg, yield: 66%).

Provenance & Evidence