Thesis-Final 03 June 2011 pdf - Jacobs University

Annex Chapter 6
(1S, 3R, 4R, 5R)-1, 3, 4-tri-(dimethoxycinnamoyl) quinide, (105)
To a solution of quinide (0.500 g, 2.871 mmol) and N,N-(dimethylamino)pyridine
(0.002 g, 0.140 mmol) in dichloromethane (5 ml) was added triethylamine (1.4 ml)
followed by the addition of 3,4-dimethoxycinnamic acid chloride (2.275 g, 10.048
mmol). The reaction mixture was stirred for 12 hours at room temperature under a
nitrogen atmosphere. Dichloromethane (2x30 ml) and 2M HCl (20 ml) were added to
solution and the organic layer was separated. The organic layer was then dried over
MgSO 4 and filtered. The solvent was removed under reduced pressure. The residue
was purified by recrystallisation from EtOH to give the title compound (105) as a
slightly yellow powder (1.780 g, 84%). Rf 0.75 [ethyl acetate: petrol ether (2:3)]; mp
125 °C; IRν max (Nujol)/cm -1 : 2840 (C-H), 1758, 1756, 1713 (C=O), 1627, 1599
(C Ar =C Ar ), 1267, 1243, 1156, 1077 (C-O); δ H (500 MHz, CDCl 3 ): 2.52 (1 H, m, 2-
H ax ), 2.65 (1 H, t, J 11.5, 6-H ax ), 2.89 (1 H, d, J 11.5, 2-H eq ), 3.14 (1 H, m, 2-H ax ),
3.80 (3 H, s, 35-H), 3.88 (3 H, s, 36-H), 3.90 (3 H, s, 37-H), 3.91 (3 H, s, 38-H), 3.92
(1 H, s, 39-H), 3.96 (1 H s, 40-H), 5.02 (1 H, t, J 5, 5-H), 5.38 (1 H, m, 3-H), 5.73 (1
H, t, J 4.5, 4-H), 6.22 (1 H, d, J 16, 9-H), 6.36 (1 H, d, J 16, 18-H), 6.42 (1 H, d, J
15.5, 27-H), 6.79-7.28 (9 H, m, Ph-H), 7.13 (1 H, d, J 16, 10-H), 7.58 (1 H, d, J 16,
19-H), 7.70 (1 H, d, J 15.5, 28-H); δ C (125 MHz, CDCl 3 ): 34.12 (C-2), 34.98 (C-6),
56.03 (C-35), 56.19 (C-36), 56.21 (C-37), 56.23 (C-38), 56.24 (C-39), 56.16 (C-40),
65.17 (C-4), 66.25 (C-3), 74.24 (C-5), 76.67 (C-1), 109.82 (C-12), 109.94 (C-21),
110.03 (C-30), 111.22 (C-15), 111.28 (C-24), 111.29 (C-33), 114.32 (C-9), 114.50
(C-18), 114.63 (C-27), 123.09 (C-16), 123.49 (C-25), 123.51 (C-34), 127.11 (C-11),
127.15 (C-20), 127.27 (C-29), 146.28 (C-10), 146.93 (C-19), 147.13 (C-28), 149.41
(C-13), 149.54 (C-14), 149.59 (C-22), 151.20 (C-23), 151.59 (C-31), 151.89 (C-32),
165.42 (C-8), 165.54 (C-17), 165.78 (C- 26), 171.74 (C-7); MS, m/z (CI): 744 [M + ],
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