Water → 1-Diphenylmethyl-3-(2,8-bis(trifluoromethyl)-4-quinolinyl)-3-azetidinol

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Reaction Steps

To a solution of 4-bromo-2,8-bis(trifluoromethyl)quinoline (500 mg, 1.45 mmol) in dry ether (10 mL) at −78° C. under argon was added n-butyllithium (0.64 mL of 2.5-M, 1.6 mmol). After 20 min a solution of N-diphenylmethyl-3-azetidinone (345 mg, 1.45 mmol) in ether (5 mL) was added dropwise, the mixture stirred for 20 min, water was added and the mixture allowed to warm slowly to room temperature. The mixture was extracted with ether (3×20 mL), the combined extracts dried (MgSO4), concentrated in vacuo and the residue purified by chromatography [SiO2; heptane-EtOAc (3:1)] to give the product (738 mg, 100%) as a pale yellow foam: IR νmax (Nujol)/cm−1 3378, 2924, 1456, 1377, 1311, 1145 and 702; NMR δH (400 MHz, CDCl3) 3.74-3.79 (4H, m), 4.45 (1H, s), 7.21-7.37 (6H, m), 7.41-7.46 (4H, m), 7.65-7.69 (2H, m), 8.15 (1H, d, J 7.1 Hz) and 8.35 (1H, d, J 8.6 Hz).

Provenance & Evidence