Hydrochloric Acid → HCID 67325684, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of N-(2,4-Dimethoxy-benzyl)-2-(4-ethoxy-2-oxo-cyclohex-3-enyl)-acetamide (549 mg, 1.58 mmol) in THF (10 mL) at −78° C. was added 1.0M of diisobutylaluminum hydride in heptane (2.0 mL). The reaction mixture was then stirred at 0° C. for one hour. 5 M of hydrogen chloride in water (2.0 mL) was added and the reaction mixture stirred at room temperature for 30 minutes. The reaction mixture was then partitioned between water and ethyl acetate, and the organic layer dried with brine and magnesium sulfate, filtered, and evaporated in vacuo to yield 471.8 mg (98%) of N-(2,4-Dimethoxy-benzyl)-2-(4-oxo-cyclohex-2-enyl)-acetamide which was carried forward without purification. LCMS (Method E, ESI): RT=1.23 min, m+H=304.2; 1H NMR (400 MHz, CDCl3) δ: 7.19 (d, J=8.1 Hz, 1H), 6.84 (ddd, J=10.2, 2.6, 1.3 Hz, 1H), 6.45 (dt, J=8.2, 2.2 Hz, 2H), 5.97 (dd, J=10.2, 2.1 Hz, 1H), 5.88 (s, 1H), 4.38 (d, J=5.7 Hz, 2H), 3.83 (s, 3H), 3.80 (s, 3H), 3.02 (s, 1H), 2.51-2.36 (m, 2H), 2.36-2.27 (m, 1H), 2.23 (dd, J=14.5, 7.6 Hz, 1H), 2.19-2.08 (m, 1H), 1.76-1.62 (m, 1H).

Provenance & Evidence