Acetic Anhydride → 1-Acetylamino-6,7,8,9-tetrahydro-5H-benzocycloheptene

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Reaction Steps

A solution of the product from Example 132A (1.6 g, 9.92 mmol) in ethanol (30 ml) was added a solution of acetic anhydride (1.872 ml, 19.85 mmol) in EtOH (30 mL) at 0° C. The mixture was stirred at room temperature for 16 hours. The mixture was concentrated under reduced pressure and the residue was taken up in EtOAc (100 mL) and the organic solution was washed with H2O, dried and concentrated. The residue was purified by chromatography on silica gel eluting with 15% EtOAc/hexanes to provide the title product. 1H NMR (CDCl3) δ 1.54-1.71 (m, 6H), 1.77-1.89 (m, 2H), 2.20 (s, 3H), 2.72-2.76 (m, J=5.55 Hz, 1H), 2.78-2.85 (m, J=10.71 Hz, 2H), 6.97-7.11 (m, 2H), 7.22 (d, 1H). MS (M+H)+ m/z 204.

Provenance & Evidence