Diisobutylaluminumhydride → (E)-2-Fluoro-3-(6-isopropyl-4,4-dimethyl-1-n-propyl-1,2,3,4-tetrahydro-quinolin-8-yl)-but-2-enoic acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

To a solution of (E)-3-(1-ethyl-6-isopropyl-4,4-dimethyl-1,2,3,4-tetrahydro-quinolin-8-yl)-2-fluoro-but-2-enoic acid ethyl ester (Intermediate 15, 199 mg, 0.55 mmol) in 10 ml of anhydrous THF under argon at 0° C. was added a 1.0 M solution of diisobutylaluminum hydride (2.20 ml, 2.20 mmol) in hexanes. The resulting mixture was stirred at 0° C. to 25° C. for 1 h. The reaction was cooled to 0 ° C. and quenched slowly with saturated NH4Cl (0.5 ml), Celite (200 mg), and diluted with diethyl ether (10 ml). The resulting mixture was stirred at 25 ° C. for 1 hour. The product was filtered through a pad of Celite. The solution was dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography using ethyl acetate: hexane (1:4) to yield the title compound as a yellow oil.

Provenance & Evidence