Molecules 2010, 15
3899
1H, OH), 6.97 (s, 1H, ArH), 7.12 (dd, J 3.1 and 2.5, 1H, H-2), 9.84 (brs, 1H, NH); 13C-NMR (acetone-
d6): δ 56.6 (OCH3), 57.6 (CH2OCH3), 67.5 (CH2OCH3), 101.0, 94.9, 123.7, 113.8, 122.7, 130.4, 140.6
and 145.7; MS (EI, 70 eV), m/z [%]: 207 (46, M+), 175 (100), 161 (13), 146 (52), 132 (80), 118 (14),
104 (34), 91 (5); HR-MS for C11H13NO3; calcd. 207.0895, found: 207.0886.
3.1.8. 4-Methoxy-6-(methoxymethyl)-5-(oxiran-2-ylmethoxy)-1H-indole (8) and 6-methoxy-4-
(methoxymethyl)-5-(oxiran-2-ylmethoxy)-1H-indole (9)
Indole derivatives 6 and 7 were treated with (+/-)-epichlorohydrin in the presence of a
stoichiometric quantity of base in dioxane and water according to the procedure described in the
literature [1], to give the epoxides 8 and 9 with yields of 44% and 64%, respectively, as oils of
chromatographic purity.
Product 8: IR: 735.9, 1046.1, 1239.3, 1354.2, 1436.5, 1444.6, 1496.7, 1734.1, 2929.0, 3350.4 (NH)
cm-1; 1H-NMR (CDCl3): δ 2.71 and 2.87 (part AB of ABX system, JAB −4.9, 4.6 and 2.7, 2H, H-10),
3.38–3.41 (m, 1H, H-9), 3.44 (s, 3H, CH2OCH3), 3.98 (dd, J −11.2 and 6.3, 1H, H-8), 4.06 (s, 3H,
OCH3), 4.27 (dd, J −11.2 and 3.2, 1H, H-8), 4.61 (AB system, J 11.6, 2H, CH2OCH3), 6.59–6.60 (m,
13
1H, H-3), 7.09 (s, 1H, H-7), 7.09–7.10 (m, 1H, H-2), 8.40 (brs, 1H, NH); C-NMR (CDCl3): δ 44.6
(C10), 50.8 (C9), 58.2 (CH2OCH3), 60.5 (OCH3), 70.6 (CH2OCH3), 74.9 (C8), 100.0 (C3), 106.5 (C7),
124.5 (C2), 121.4, 127.1, 134.0, 141.7, 144.9 (C-3a, 4, 5, 6, 7a); MS (EI, 70 eV), m/z [%]: 263 (48,
M+), 206 (100), 191 (11), 176 (48), 147 (18), 132 (26), 118 (13); HR-MS for C14H17N1O4; calcd.
263.1158, found: 263.1165.
Product 9: IR: 728.7, 846.8, 1086.0, 1143.9, 1199.2, 1301.1, 1459.5, 2924.5, 3369.9 (NH) cm-1;
1H-NMR (CDCl3): δ 2.70 and 2.86 (part AB of ABX system, JAB −5.0, 4.3 and 2.7, 2H, H-10),
3.38–3.41 (m, 1H, H-9), 3.42 (s, 3H, CH2OCH3), 3.80 (s, 3H, OCH3), 3.96 (dd, J −11.1 and 6.1, 1H,
H-8), 4.18 (dd, J −11.1 and 3.5, 1H, H-8), 4.84 (AB system, J 10.8, 2H, CH2OCH3), 6.57–6.58 (m, 1H,
13
H-3), 6.79 (s, 1H, H-7), 7.03 (dd, J 3.1 and 2.6, 1H, H-2), 8.47 (brs, 1H, NH); C-NMR (CDCl3): δ
44.7 (C10), 50.6 (C9), 56.0 (OCH3), 58.1 (CH2OCH3), 67.1 (CH2OCH3), 75.1 (C8), 95.0 (C7), 101.0
(C3), 123.5 (C2), 121.4, 122.0, 132.3 (C-3a, 4, 7a), 141.6 (C5), 149.5 (C6); MS (EI, 70 eV), m/z [%]:
263 (M+, 100), 206 (98), 191 (15), 190 (23), 178 (51), 175 (32), 163 (22), 147 (35), 132 (30), 118 (34),
116 (34), 104 (20); HR-MS for C14H17NO4; calcd. 263.1158, found: 263.1148.
3.1.9. (2R,S)-1-(4-Methoxy-6-(methoxymethyl)-1H-indol-5-yloxy)-3-(2-(2-methoxyphenoxy)ethyl
amino)propan-2-ol (10) and (2R,S)-1-(6-methoxy-4-(methoxymethyl)-1H-indol-5-yloxy)-3-(2-(2-
methoxyphenoxy)ethylamino)propan-2-ol (11)
Compounds 8 and 9 were converted into the final products 10 and 11 using the procedure described
in the literature [1]. They were obtained as foams with yields of 70% and 68%, respectively.
Compound 10: IR: 1023.5, 1053.1, 1223.8, 1250.8, 1353.4, 1453.3, 1503.4, 3350.5 (NH and OH) cm-1;
1H-NMR (CDCl3): δ 2.17 (brs, 2H, OH and NH), 2.82–2.88 (m, 2H, H-3), 3.08 (t, J 5.5, 2H, H-4), 3.38
(s, 3H, OCH3), 3.83 (s, 3H, OCH3), 4.01 (dd, J 6.9 and 3.2, 1H, H-1), 4.04 (s, 3H, OCH3), 3.99–4.02
(m, 1H, H-2), 4.14 (t, J 5.5, 2H, H-5), 4.26 (dd, J 7.5 and 2.7, 1H, H-1), 4.58 (s, 2H, H-20), 6.59–6.60