Dimethylacetamide → (1S,2S)-N,N-dimethyl-(6-fluoro-2-hydroxy-1-isopropyl-1, 2,3,4-tetrahydronaphthalen-2-yl)acetamide

Participants

Reaction Conditions

Reaction Steps

Lithium diisopropylamide, 1.3 mL of 0.84 molar solution in tetrahydrofuran, was added to a solution of 0.11 mL N,N-dimethylacetamide in 1 mL tetrahydrofuran at -78° C. The mixture was stirred for fifteen minutes, then allowed to warm to -55° C. A solution of 220 mg (S)-6-fluoro-1-isopropyl-3,4-dihydro-1H-naphthalen-2-one in 1 mL tetrahydrofuran was added at that temperature, then allowed to warm to 0-5° C. with stirring, and stirred for 2.5 hours. The reaction mixture was quenched with 3 mL saturated aqueous ammonium chloride, and extracted three times with 3 mL portions of diethyl ether. The ether extracts were combined, dried with magnesium sulfate, and stripped to give 290 mg (1S,2S)-N,N-dimethyl-(6-fluoro-2-hydroxy-1-isopropyl-1, 2,3,4-tetrahydronaphthalen-2-yl)acetamide as a pale yellow oil.

Provenance & Evidence