Ethyl trans-crotonate → HCID 11789974, compound

Participants

Reaction Steps

To a stirred solution of 20.394 g (96.513 mmol) of (S)-alpha-methyl-N-(phenylmethyl)-benzenemethanamine (from Example 5) in 400 mL of THF, cooled to 0° C., was added, over a 10 minute period, 38.61 g (96.525 mmol) of n-butyllithium, and the reaction was stirred for an additional 15 minutes. To this solution was added 10.00 mL (80.427 mmol) of ethyl crotonate with stirring over a 20 minute period, and the solution was stirred for an additional 20 minutes. The reaction was quenched by addition of an excess of saturated ammonium chloride solution, and the mixture was extracted with ether. The ether extract was washed with saturated brine, dried over MgSO4 and concentrated to give a colorless liquid. The crude product was chromatographed on silica gel, eluting with 1:4 ethyl acetate:hexane, and the solvent was removed to afford 24.10 g (92.1%) of the title product as a colorless oil. MS M/Z: 326 (M+H). NMR (CDCl3) δ: 1.13 (d, 3 H, J=7 Hz), 1.16 (t, 3H, J=7 Hz), 1.35 (d, 3H, J=7 Hz), 2.10 (dd, 1H, J=14 Hz, J=6 Hz), 2.36 (dd, 1H, J=14 Hz, J=6 Hz), 3.44 (m, 1H), 3.67 (d, 1H, J=14 Hz), 3.74 (d, 1H, J=14 Hz), 3.88-4.07 (m, 3H), 7.19-7.42 (10H). Anal calc. for C21H27NO2 : C, 77.50; H, 8.36 N, 4.30; found: C, 77.46; H, 8.37; N, 4.28.

Provenance & Evidence