Acetic Acid → (3-{(R)-3-[(2-Chloro-3-trifluoromethyl-benzyl)-((S)-2-phenyl-propyl)-amino]-butoxy}-phenyl)-acetic Acid Methyl Ester

Participants

Reaction Steps

To a solution of {3-[(R)-3-((S)-2-Phenyl-propylamino)-butoxy]-phenyl}-acetic acid methyl ester (0.12 g, 0.34 mmol) in dry dichloromethane was added acetic acid followed by 2-chloro-3-trifluoromethylbenzaldehyde (0.1 g, 0.51 mmol) and sodium triacetoxyborohydride (0.149, 0.68 mmol). After the resulting mixture was stirred at room temperature overnight water was added to quench the reaction. The aqueous layer was extracted with ethyl acetate. The combined organic layers was washed with brine, dried over sodium sulfate and concentrated in vacco. The crude mixture was purified by silica gel column chromatography using EtOAc:Hexane/25:75 as the eluent to give 50 mg (40% yield) of the title compound as an oil MS m/e 548.4 (M+H)+.

Provenance & Evidence