Tetrapropylammonium → 2-(3,4-Dichloro-phenyl)-3-(3-oxo-cyclopentyl)-propionic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-(3,4-dichloro-phenyl)-3-(3-hydroxy-cyclopentyl)-propionic acid methyl ester (prepared as in Example 36, 356.4 mg, 1.12 mmol), N-methylmorpholine N-oxide (197 mg, 1.68 mmol), and powdered molecular sieves (1.12 g) in methylene chloride (2.25 mL) at 25° C. was treated with tetrapropylammonium perrhuthenate (20 mg, 0.05 mmol). The resulting mixture was stirred at 25° C. for 30 min. At this time, the reaction was filtered through a pad of celite (ethyl acetate as eluent). The filtrate was concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230–400 mesh, 75/25 hexanes/ethyl acetate) afforded 2-(3,4-dichloro-phenyl)-3-(3-oxo-cyclopentyl)-propionic acid methyl ester (261.3 mg, 73.8%) as a clear oil: EI-HRMS m/e calcd for C15H16Cl2O3 (M+Na)+ 337.0370, found 337.0371.

Provenance & Evidence