Diisopropylethylamine → cis-3-Benzyl-1-(4-methoxyphenylsulfonyl)-4-phenyl-3,4-dihydropyridin-2(1h)-one

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Reaction Steps

The title compound was prepared according to the general procedure from 2-chloro-3-phenylpropanal and trans-N-(4-methoxybenzenesulfonyl)-3-phenyprop-2-ene-1-imine using 10 mol % 7 and 1.5 equiv DIPEA in 40% yield. 1H NMR (400 MHz, CDCl3) δ 8.02 (dd, 2H, J=7.0, 2.1 Hz), 7.24-7.10 (m, 4H), 7.09-6.94 (m, 7H), 6.47 (dd, 2H, J=8.0, 1.0 Hz), 5.48 (dd, 1H, J=8.0, 6.3 Hz), 3.90 (s, 3H), 3.33-3.30 (m, 1H), 3.27-3.21 (m, 1H), 3.15 (dd, 1H, J=14.6, 4.3 Hz), 2.10 (dd, 1H, J=14.6, 9.0 Hz); 13C NMR (100 MHz, CDCl3) δ 170.2, 164.3, 138.8, 137.4, 131.5, 129.2, 129.1, 128.8, 128.7, 128.2, 127.7, 126.6, 124.1, 114.4, 114.3, 56.0, 48.9, 41.1, 31.5; IR (thin film) ν 3062, 3029, 2926, 1721, 1594, 1496, 1362, 1263, 1167, 1091, 1027 cm−1; HRMS (ESI) calcd for C25H23NO4S [M+Na]+ XX, found XX.

Provenance & Evidence