HCID 86696501, compound → HCID 1490683, compound

Participants

Reaction Steps

Methylmagnesium bromide (0.717 mL, 3M in ether, 2.150 mmol) was added dropwise to a 0° C. solution of (1S,2S)-2-(4-fluorophenyl)-N-methoxy-N-methyl cyclopropanecarboxamide (400 mg, 1.792 mmol) in THF (15 mL). After 2 h, an additional equivalent of methylmagnesium bromide (0.717 mL, 2.150 mmol) was added. The reaction was slowly quenched with sat'd ammonium chloride (2 mL). The mixture was diluted with EtOAc, washed with H2O, washed with brine, dried over magnesium sulfate, and concentrated to give (1S,2S)-1-(2-(4-fluorophenyl)cyclopropyl)ethanone as a slightly colored oil (304 mg, 95%). 1H NMR (500 MHz, CHLOROFORM-d) δ 7.12-7.04 (m, 2H), 7.03-6.95 (m, 2H), 2.53 (ddd, J=9.1, 6.5, 4.0 Hz, 1H), 2.37-2.30 (m, 3H), 2.18 (ddd, J=8.2, 5.1, 4.0 Hz, 1H), 1.67 (ddd, J=9.2, 5.1, 4.3 Hz, 1H), 1.35 (ddd, J=8.1, 6.6, 4.3 Hz, 1H).

Provenance & Evidence