Acetone → HCID 15454096, compound

Participants

Reaction Steps

To a solution of 4-[(1,1,3,3-tetramethyl-1,3-dihydro-isobenzofuran-5-yl)-amino]-benzoic acid ethyl ester (Compound 79, 0.1 g, 0.32 mmol) and sodiumcyanoborohydride (0.12 g, 1.92 mmol) in 2 mL of acetone and 2 mL of acetic acid, sodiumcyanoborohydride (0.1 g, 1.58 mmol) was added followed by a drop of sulfuric acid. After half an hour at room temperature, another drop of sulfuric acid was added and the reaction mixture was stirred at room temperature for 3 days. The reaction mixture was taken up in ethyl acetate and washed with brine. The organic phase was dried over anhydrous sodium sulfate, filtered and evaporated to a residue which was subjected to flash column chromatography on silica gel, using 5% ethyl acetate in hexane as the eluent, to afford the title compound (0.007 g, <10%). 1H NMR (300 MHz, CDCl3): δ 7.83 (d, 2H, J=9.0 Hz), 7.14 (d, 1H, J=7.9 Hz), 7.00 (dd, 1H, J=7.8, 1.8 Hz), 6.81 (d, 1H, J=1.7 Hz), 6.52 (d, 2H, J=9.2 Hz), 4.39 (heptet, 1H, J=6.6 Hz), 4.30 (q, 2H, J=7.11 Hz) 1.56 (s, 6H), 1.51 (s, 6H), 1.34 (t, 3H, J=7.1 Hz), 1.17 (d, 6H, J=6.6 Hz).

Provenance & Evidence