One-Pot Synthesis of α-Aminophosphonates: An Inexpensive Approach

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• TYPICAL EXPERIMENTAL PROCEDURE; To a stirred solution of the aldimine (generated in situ from the corresponding aldehyde and the amine Table 1) (5 mmol) in acetonitrile (10 mL) was added trimethyl phosphite (6 mmol) and AlCl3 (10 mol%). The reaction mixture was stirred at RT (Table 1), i.e., till the completion of the reaction as indicated by the TLC. The reaction mixture was quenched with water. The solid samples were separated by filtration and recrystallised, otherwise the reaction mixture was extracted with EtOAc (2 × 20 mL) dried over anhydrous sodium sulfate, concentrated in vacuo and purified by column chromatography (hexane:ethyl acetate, 80:20). All the compounds gave satisfactory spectral (1H NMR) and analytical data (C, H, and N). Selected spectral data for few compounds is given below. 4b: M.p. 72–74°C; 1H NMR (200°MHz, CDCl3): δ 3.41–3.61 (d, 3H); 3.62–3.82 (d, 3H); 4.60–4.82 (d, 1H); 6.50–6.59 (d, 1H); 6.59–6.78 (t,1H) 6.98–7.45 (m, 12H). Anal. calcd. For C21H22NO4P: C-65.80; H-5.74; N-3.66; found. C-65.84; H-5.72; N-3.60. 4d: M.p. 92–94°C; 1H NMR (200°MHz, CDCl3): δ 3.48–3.68 (d, 3H); 3.69–3.89 (d, 3H); 4.90–5.29 (d, 1H); 6.58–6.82 (m, 3H); 6.90–7.35 (m, 5H). Anal. calcd. For C13H16NO3SP: C-52.52; H-5.39; N-4.71; found. C-52.66; H-5.30; N-4.72. 4e: M.p. 98–100°C; 1H NMR (300 MHz, CDCl3): δ 3.54–3.65 (d, 3H), 3.69–3.81 (d, 3H), 5.28 (bs, 1H), 5.70–5.90 (d, 1H), 6.54–6.62 (d, 2H,); 6.63–6.75 (t, 1H) 7.02–7.40 (m, 5H). Anal. calcd. For C15H16Cl2NO3P: C-50.0; H-4.4; N-3.89; found. C-49.5; H-4.47; N-3.85. 4g: M.p. 118–120°C; 1H NMR (300°MHz, CDCl3): δ 3.40–3.50 (d, 3H), 3.70 (s, 3H), 3.75–3.85 (d, 3H), 3.90 (s, 3H), 4.65 –4.81(b, 1H), 5.24–5.40 (dd, 1H), 6.50–6.60 (d, 1H), 6.61–6.68 (t, 1H), 6.69–6.76 (t, 1H), 6.76–6.86 (d, 1H), 6.91–7.21 (m, 4H). Anal. calcd. For C17H22NO5P: C-58.12; H-6.30; N-3.99; found. C-58.07; H-6.29; N-3.93. 4i: M.p. 152–4°C; 1H NMR (200 MHz, CDCl3): δ 3.32–3.52 (d, 3H), 3.56–3.76 (d, 3H), 5.20–5.40 (bm, 1H), 5.42–5.62 (d, 1H), 6.62–6.38 (d, 1H, CH), 6.38–6.52 (t, 1H) 6.68–6.80 (d, 2H, Ar), 7.14–7.38 (d, 3H, Ar), 7.88–8.00 (s, 1H). Anal. calcd. For C15H19N2O4P: C-55.90; H-5.95; N-8.70; found. C-55.75; H-5.95; N-8.73
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