N, N-Dibenzyl Formamide Dimethyl Acetal and N, N-Dibenzyl Chloromethylene Iminium Chloride: Two Complementary Reagents for the Protection Of Primary Amines as N, N-Dibenzyl Formamidines

References

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• Selected spectral data. (3) : 1. H‐NMR (CDC13, 300 MHz) δ 7.86 (s, 1H); 7.36–7.10 (m, 10H); 4.37 (s, 4H); 3.48 (t, J = 6.4 Hz, 2H); 3.43 (t, J= 6.4 Hz, 2H); 2.11 (q, J= 6.4 Hz, 2H). (4): 1. H‐NMR (CDCl3 200 MHz) 8 7.62 (s, 1H); 7.33–7.12 (m, 10H); 4.53 (t, J= 5.1 Hz, 1H); 4.31 (s, 4H); 3.85–3.40 (m, 4H); 3.34 (t, J= 5.9 Hz, 2H); 1.70–1.62 (m, 4H); 1.25 (t, .7=6.9 Hz, 6H). (5) : 1. H‐NMR (CDC13, 300 MHz) δ 7.72 (s, 1H); 7.42–7.20 (m, 10H); 4.38 (s, 4H); 3.65 (t, J = 6.4 Hz, 2H); 3.38 (t, J= 6.6 Hz, 2H); 1.67–1.62 (m, 4H); 1.25 (q, J= 7.0 Hz, 2H). (6): 1. H‐NMR (CDC13, 200 MHz) δ 7.98 (s, 1H); 7.82–7.20 (m, 14H); 6.80–6.62 (m, 3H); 4.74 (s, 2H); 4.35 (s, 2H); 3.67 (s, 3H). (7) : 1. H‐NMR (CDC13, 300 MHz) δ 7.60 (s, 1H); 7.46–7.30 (m, 10H); 7.10 (d, J = 7.3 Hz, 2H); 6.92 (t, J= 7.3 Hz, 1H); 4.54 (s, 4H); 2.32 (s, 6H). (8, 2 diastereomers): 1. H‐NMR (CDCl3, 200 MHz) δ 8.94 and 8.93 (2s, 1H); 7.73 (s, 1H), 7.60–7.15 (m, 15H); 6.24 and 6.16 (2d, J= 2.5 Hz, 1H); 6.23 and 6.02 (2s, 1H); 5.37 (dd, J= 2.5, 6.6 Hz, 1H); 5.03 (m, 1H); 4.75–4.39 (m, 5H); 3.91 (m, 1H). (9) : 1. H‐NMR (CDCI3, 200 MHz) δ 9.37 (s, 1H); 8.55 (s, 1H); 7.96 (s, 1H); 7.42–7.10 (m, 10H); 5.89 (d, J = 5.0 Hz, 1H); 5.22 (dd, J= 5.0, 5.6 Hz, 1H); 5.10 (d, J= 5.6 Hz, 1H); 4.87 (s, 2H); 4.53 (s, 1H); 4.43 (s, 2H); 4.10–3.70 (m, 2H); 1.63 (s, 3H); 1.36 (s, 3H). (10) : 1. H‐NMR (CD3OD, 200 MHz) 89.05 (s, 1H); 8.10 (s, 1H); 7.40–7.20 (m, 10H); 5.99 (d, J= 5.9 Hz, 1H); 4.73 (dd, J= 5.5, 5.9 Hz, 1H);4.68 (s, 2H), 4.53 (s, 2H); 4.37 (dd, J= 3.3, 5.5 Hz, 1H); 4.14 (m, 1H); 3.82 (AB part of ABX syst, JAB = 122 Hz, JAX=2.7 Hz, JBX= 2.7 Hz, δv = 13.0 Hz, 2H). (11) : 'H‐NMR (CD3OD, 200 MHz) 8 9.25 (s, 1H); 8.49 (s, 1H); 7.41–7.23 (m, 8H); 7.11–7.06 (m, 2H); 5.51 (s, 2H); 4.60 (s, 4H); 3.69 (t, J= 5.7 Hz, 2H); 2.93 (t, J= 5.7 Hz); 2.62 (s, 3H); 2.43 (s, 3H)
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• The reaction can be run in anhydrous DMF with a comparable yield and without any formation of N,iV‐dimethyl formamidine
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