Ritter Reaction Mediated by Bismuth(III) Salts: One-Step Conversion of ­Epoxides into vic-Acylamino-Hydroxy Compounds

Rui M. A. Pinto; Jorge A. R. Salvador; Christophe Le Roux

doi:10.1055/s-2006-949608

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Synlett 2006(13): 2047-2050
DOI: 10.1055/s-2006-949608

LETTER

Ritter Reaction Mediated by Bismuth(III) Salts: One-Step Conversion of Epoxides into vic-Acylamino-Hydroxy Compounds

Rui M. A. Pinto^a, Jorge A. R. Salvador*^a, Christophe Le Roux^b
^a Laboratório de Química Farmacêutica, Faculdade de Farmácia, Universidade de Coimbra, 3000-295, Coimbra, Portugal
Fax: +351(239)827126; e-Mail: salvador@ci.uc.pt;
^b Laboratoire Hétérochimie Fondamentale et Appliquée, 118, Route de Narbonne, 31062 Toulouse Cedex 9, France

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Publication History

Received 17 April 2006
Publication Date:
09 August 2006 (online)

Abstract
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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

References and Notes

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19

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.