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DOI: 10.1055/s-2006-949608
Ritter Reaction Mediated by Bismuth(III) Salts: One-Step Conversion of Epoxides into vic-Acylamino-Hydroxy Compounds
Publikationsverlauf
Publikationsdatum:
09. August 2006 (online)
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Abstract
Bismuth salts promote a new one-step conversion of epoxides into vic-acylamino-hydroxy compounds in very high yields.
Key words
bismuth salts - epoxides - steroids - ring opening - vic-acylamino-hydroxy compounds
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References and Notes
Selected Data.
Compound 2: 1H NMR (300 MHz, CDCl3): δ = 0.69 (3 H, s, 18-H3), 1.12 (3 H, s, 19-H3), 2.01 (3 H, s, CH3COO), 2.02 (3 H, s, CH3CONH), 4.02 (1 H, m, 6α-H), 5.16 (1 H, m, 3α-H), 5.60 (1 H, d, J = 9.7 Hz, NH). 13C NMR (75.5 MHz, CDCl3): δ = 70.9 (C3), 75.5 (C5), 169.5 (CONH), 170.5 (COO). IR (ATR): 3394, 2934, 2870, 1734, 1716, 1662, 1514, 1374, 1245, 1029 cm-1.
Compound 4: 1H NMR (300 MHz, CDCl3): δ = 0.90 (3 H, s, 18-H3), 1.16 (3 H, s, 19-H3), 2.02 (3 H, s, CH3COO), 2.05 (3 H, s, CH3CONH), 4.12 (1 H, m, 6α-H), 5.16 (1 H, m, 3α-H), 5.66 (1 H, d, J = 9.7 Hz, NH). 13C NMR (75.5 MHz, CDCl3): δ = 70.6 (C3), 75.4 (C5), 169.6 (CONH), 170.5 (COO), 220.7 (C17). IR (ATR): 3370, 2938, 2875, 1735, 1711, 1648, 1532, 1367, 1257, 1028 cm-1.
Compound 6: 1H NMR (300 MHz, CDCl3): δ = 0.64 (3 H, s, 18-H3), 1.12 (3 H, s, 19-H3), 2.02 (3 H, s, CH3COO), 2.02 (3 H, s, CH3CONH), 2.12 (3 H, s, 21-H3), 4.08 (1 H, m, 6α-H), 5.17 (1 H, m, 3α-H), 5.64 (1 H, d, J = 9.7 Hz, NH). 13C NMR (75.5 MHz, CDCl3): δ = 70.8 (C3), 75.4 (C5), 169.6 (CONH), 170.6 (COO), 209.6 (C20). IR (ATR): 3381, 2940, 2870, 1728, 1701, 1654, 1533, 1364, 1246, 1030 cm-1. ES-MS: m/z (%) = 434 (100) [M]+, 416 (37), 374 (20), 356 (30). Anal. Calcd for C25H39NO5: C, 69.25; H, 9.07; N, 3.23. Found: C, 69.01; H, 9.27; N, 3.38.
Compound 8: 1H NMR (300 MHz, CDCl3): δ = 0.68 (3 H, s, 18-H3), 1.11 (3 H, s, 19-H3), 2.00 (3 H, s, CH3CONH), 3.98-4.19 (2 H, m, 3α-H and 6α-H), 5.69 (1 H, d, J = 10.1 Hz, NH). 13C NMR (75.5 MHz, CDCl3): δ = 67.2 (C3), 75.8 (C5), 169.6 (CONH). IR (ATR): 3460, 3437, 2933, 2867, 1650, 1523, 1378, 1046 cm-1.
Compound 10: 1H NMR (300 MHz, CDCl3): δ = 1.03 (3 H, s, 15-H3), 2.00 (3 H, s, CH3CONH), 3.29 (1 H, m, 9α-H), 4.14 (1 H, m, 2α-H), 5.54 (1 H, d, J = 9.2 Hz, NH). 13C NMR (75.5 MHz, CDCl3): δ = 57.7 (C2), 74.9 (C9), 169.8 (CONH). IR (ATR): 3480, 3306, 2942, 2864, 1623, 1557, 1462, 1447, 1376, 1047 cm-1.
Compound 11: 1H NMR (300 MHz, CDCl3): δ = 0.69 (3 H, s, 18-H3), 1.27 (3 H, s, 19-H3), 1.97 (3 H, s, CH3COO), 4.27 (1 H, m, 6α-H), 5.18 (1 H, m, 3α-H), 6.28 (1 H, d, J = 9.7 Hz, NH), 7.44-7.58 (3 H, m, Ar), 7.72-7.78 (2 H, m, Ar). 13C NMR (75.5 MHz, CDCl3): δ = 70.7 (C3), 166.6 (CONH), 170.6 (COO). IR (ATR): 3463, 2936, 2862, 1729, 1717, 1654, 1575, 1516, 1477, 1364, 1240, 1030 cm-1.
Compound 13: 1H NMR (300 MHz, CDCl3): δ = 0.90 (3 H, s, 18-H3), 1.35 (3 H, s, 19-H3), 2.01 (3 H, s, CH3COO), 2.01 (3 H, s, CH3CONH), 4.76 (1 H, m, 6α-H), 4.84 (1 H, m, 3α-H), 5.25 (1 H, s, NH). 13C NMR (75.5 MHz, CDCl3): δ = 71.2 (C3), 170.1 (CONH), 171.2 (COO), 221.3 (C17). IR (ATR): 3451, 3407, 2941, 1735, 1721, 1658, 1507, 1375, 1239, 1026 cm-1.
Compound 14: 1H NMR (300 MHz, CDCl3): δ = 0.70 (3 H, s, 18-H3), 1.28 (3 H, s, 19-H3), 2.04 (3 H, s, CH3COO), 3.83 (1 H, m, 6α-H), 5.11 (1 H, m, 3α-H). 13C NMR (75.5 MHz, CDCl3): δ = 64.0 (C6), 71.1 (C3), 76.4 (C5), 171.0 (COO). IR (ATR): 3384, 2933, 1735, 1697, 1457, 1363, 1267, 1245, 1030, 687 cm-1.