Acetic Acid → Ethyl 4-[(1-isopropyl-4,4-dimethyl-1,2,3,4-tetrahydro-quinolin-7-yl)(cyclopropylmethyl)amino]benzoate

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Reaction Steps

A solution of 4-[(1-isopropyl-4,4-dimethyl-1,2,3,4-tetrahydroquinolin-7-yl)amino]benzoate (Compound 34, 9.4 mg, 0.0256 mmol), cyclopropylcarboxaldehyde (8.99 mg, 0.1282 mmol), sodium cyanoborohydride (8.06 mg, 0.1282 mmol), acetic acid (0.125 mL), and acetonitrile (1 mL) was stirred at room temperature for 3 days. The solvent was removed and the residue was purified by silica gel chromatography (10% ethyl acetate in hexane, Rf=0.48) to give the title compound (8.03 mg, 75%) as a solid: PNMR (300 MHz, CDCl3): δ0.19 (m, 2 H), 0.49 (m, 2 H), 1.16 (d, 6 H, J=6.5 Hz), 1.30 (s, 6 H), 1.35 (t, 3 H, J=7.1 Hz), 1.73 (t, 2 H, J=6.0 Hz), 3.17 (t, 2 H, J=6.0 Hz), 3.56 (d, 2 H, J=6.5 Hz), 3.99 (sp, 1 H, J=6.6 Hz), 4.31 (q, 2 H, J=7.1 Hz), 6.43 (dd, 1 H, J=8.1, 2.0 Hz), 6.53 (d, 1 H, J=3.6 Hz), 7.71 (d, 2 H, J=9.0 Hz), 7.18 (d, 1 H, J=8.0 Hz), 7.83 (d, 2 H, J=9.0 Hz).

Provenance & Evidence