Sodium hydride → HCID 67324479, compound

Participants

Reaction Steps

To a solution of N-(2,4-Dimethoxy-benzyl)-2-(4-oxo-cyclohex-2-enyl)-acetamide (469.8 mg, 1.549 mmol) in THF (15 mL) was added sodium hydride (60 wt % on mineral oil, 245 mg, 6.12 mmol). The reaction mixture was stirred at room temperature for one hour and then quenched with saturated aqueous ammonium chloride. The mixture was then extracted twice with dichloromethane, and the combined extracts dried over magnesium sulfate, filtered, and evaporated in vacuo. Purification by column chromatography on silica gel (gradient: 0 to 10% methanol in dichloromethane) yielded 365.0 mg (78%) of 1-(2,4-Dimethoxy-benzyl)-hexahydro-indole-2,6-dione. LCMS (Method E, ESI): RT=1.22 min, m+H=304.2; 1H NMR (400 MHz, CD3OD) δ: 7.11 (d, J=8.3 Hz, 1H), 6.53 (d, J=1.8 Hz, 1H), 6.48 (dd, J=8.3, 2.1 Hz, 1H), 4.72 (d, J=14.8 Hz, 1H), 4.04 (d, J=14.8 Hz, 1H), 3.88 (dd, J=13.3, 6.7 Hz, 1H), 3.81 (s, 3H), 3.78 (s, 3H), 2.77-2.59 (m, 4H), 2.38-2.21 (m, 3H), 2.10 (dd, J=13.8, 7.8 Hz, 1H), 1.82 (dd, J=13.3, 6.2 Hz, 1H).

Provenance & Evidence