Sulfuric acid magnesium salt (1:1) → 1-Acetylamino-6,7,8,9-tetrahydro-5H-benzocycloheptene-9-one

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Reaction Steps

A solution of the product from Example 132B (1 g, 4.92 mmol) in acetone (150 ml) was added 15% MgSO4 (15 mL). To the solution was added KMnO4 (1.944 g, 12.30 mmol) and stirred at ambient temperature for 2 hours. Then heated at slightly reflux for 40 hours. The mixture was filtered through diatomaceous earth, and washed with CH2Cl2. The organic was separated, diluted with CH2Cl2, washed with saturated Na2S2O3, dried and concentrated. The residue was purified by chromatography on silica gel column eluting with 20% EtOAc/hexanes to provide the title product. 1H NMR (DMSO-d6) δ 1.68-1.74 (m, 4H), 1.94 (s, 3H), 2.55-2.59 (m, 2H), 2.70 (t, J=6.04 Hz, 2H), 6.98 (d, J=7.34 Hz, 1H), 7.22 (d, J=7.34 Hz, 1H), 7.32 (t, J=7.70 Hz, 1H), 9.90 (s, 1H). MS (M+H)+ m/z 218.

Provenance & Evidence