2-(3-Bromo-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionic acid methyl ester → 2-(3-Cyano-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-(3-bromo-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionic acid methyl ester (prepared as in Example 72, 990.0 mg, 2.54 mmol) and copper(I) cyanide (273.3 mg, 3.05 mmol) in dry N,N-dimethylformamide (2.5 mL) was heated under reflux for 4 h. The reaction was allowed to cool to 25° C., and the crude reaction mixture was directly purified without further chemical work-up. Flash chromatography (Merck Silica gel 60, 70–230 mesh, 100% hexanes then 3/1 hexanes/ethyl acetate) afforded 2-(3-cyano-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionic acid methyl ester (646.5 mg, 76%) as a very light yellow oil: EI-HRMS m/e calcd for C17H21NO4S (M+) 335.1191, found 335.1185.

Provenance & Evidence