Reaktion #1869155
ord-04d741497f364ad9b516fc50990e2c22
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The procedure for the preparation of C4-HSL was used for this series of molecules. The EDC-mediated coupling of butyric acid and trans-2- amino-cyclopentanol or trans-2-amino-cyclohexanol afforded 6 in 66% yield or 8 in 82% yield. 6: IR (KBr) 3284, 2960, 1643, 1567, 1058 cm−1; 1H NMR (500 MHz, CDCl3) δ 0.952 (t, J=7.5 Hz, 3H), 1.40-1.50 (m, 1H), 1.60-1.74 (m, 4H), 1.75-1.82 (m, 1H), 1.96-2.08 (m, 1H), 2.08-2.18 (m, 1H), 2.19 (t, J=7 Hz, 2H), 3.80-3.86 (m, 1H), 3.92-4.00 (m, 1H), 4.90 (s, 1H), 6.28 (s, 1H); 13C (125 MHz, CDCl3) δ 13.6, 19.0, 21.1, 30.0, 32.3, 38.0, 60.5, 79.5, 175.3; EI-HRMS calc'd for C9H17O2N (M+) 171.1254. found 171.1257. 8: IR (KBr) 3294, 2930, 1638, 1567, 1086, 1072 cm−1; 1H NMR (500 MHz, CDCl3): 0.952 (t, J=7.5 Hz, 3H), 1.15-1.20 (m, 4H), 1.60-1.80 (m, 4H), 1.98 (m, 2H), 2.20 (t, J=7.5, 2H), 3.30-3.34 (m, 1H), 3.54-3.60 (m, 1H), 4.20 (s, 1H), 6.30 (d, J=7 Hz, 1H); 13C (125 MHz, CDCl3) δ 13.5, 19.1, 24.0, 24.4, 31.3, 34.3, 38.4, 55.6, 74.8, 174.9; EI-HRMS calc'd for C10H19O2N (M+) 185.1410. found 185.1410.