A Convenient Synthesis Of (L)-β-Cyclopropylalanine

References

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• Selected spectral data: 1H and 13C NMR spectra were recorded at 250 MHz and 62.5 MHz respectively on a Bruker ARX-250 spectrometer. Resonances are reported in δ ppm relative to internal standards TMS (0.00 ppm) or for aqueous samples, dioxane (1H NMR 3.53, 13C NMR 66.5). 2. 1H NMR (CDCl3) δ 0.12 (m, 2H), 030 (m, 2 H), 1.00 (m, 1 H), 2.65 (d, 1 H, OH), 3.34 (d, J 7, 2 H) 13C (CDCl3) δ 2.9 (t), 13.1 (d), 67.1 (t). 3. 1H NMR (CDCl3) δ 0.34 (m, 2 H), 0.74 (2 H, m), 1.20–1.35 (m, 1 H), 3.32 (d, J 7.5, 2 H). 13C NMR (CDCl3) 7.89 (t), 14.36 (d), 39.91 (t). 4. 1H NMR (CDCl3) δ -0.01 (m, 2 H), 0.36 (m, 2 H), 0.43–0.56 (m, 1 H), 1.21 (t, J 7.2, 6 H), 2.01 (s, 3 H), 2.22 (d, J 6.6, 2 H), 4.20 (m, 4 H), 6.88 (s, 1 H, NH). 13C NMR (CDCl3) δ 3.66 (t), 5.54 (d), 13.91 (q), 22.97 (q), 36.71 (t), 62.35 (t), 66.64, 168.18, 168.84. 5. 1H NMR (D2O, neutral) δ 0.0 (m, 2 H), 0.38 (m, 2 H), 0.60 (m, 1 H), 1.82 (d, J 6.9, 2 H), 1.93 (s, 3 H); In basic D2O, resonance at 1.82 shifts to 1.98. 6. 1H NMR (D2O) δ -0.11 (m, 2H), 0.22 (m, 2 H), 0.50 (m, 1 H), 1.40 (m, 2 H), 1.81 (s, 3 H), 3.98 (AXY, J 5.4, 7.6, 1 H); (D2O/NaOD) -0.12 (m, 2 H), 0.23 (m, 2 H), 0.51 (m, 1 H), 1.41 (m, 2 H), 1.82 (s, 3 H), 3.96 (AXY, J 5.35, 7.85, 1 H); (D2O/DCl) 0.00 (m, 2 H), 0.35 (m, 2 H), 0.66 (m, 1 H), 1.58 (m, 2 H), 1.93 (s, 3 H), 4.26 (t, J 5.7, 1 H). 13C NMR (D2O) 3.20 (t), 3.80 (t), 7.20 (d), 21.90 (d), 23.30 (q), 36.50 (t), 173.30, 179.31; (D2O/NaOD) 3.30 (t), 3.80 (t), 7.30 (d), 21.80 (d), 23.50 (q), 36.40 (t), 173.40, 179.40; (D2O/DCl) 3.30 (t), 3.80 (t), 6.90 (d), 20.60 (d), 21.70 (q), 35.50 (t), 173.90, 176.50. 7. 1H NMR (D2O, neutral) δ 0.05 (m, 2 H), 0.43 (m, 2 H), 0.75 (m, 1 H), 1.68 (t, J 6.9, 2 H), 3.70 (t, J 6, 1 H); (D2O/NaOD) δ -0.15 (m, 2 H), 0.21 (m, 2 H), 0.47 (m, 1 H), 1.15–1.41 (m, 2 H), 3.08 (t, J 6.1, 1 H); (D2O/DCl) δ -0.03 (m, 2 H), 0.34 (m, 2 H), 0.56 (m, 1 H), 1.53–1.82 (ca dt, 2 H), 3.97 (t, J 5.7, 1 H). 13C NMR (D2O)δ 6.10 (t), 6.43 (t), 8.71 (d), 37.68 (t), 57.97 (d), 177.50; (D2O/NaOD) 3.34 (t), 3.46 (t), 6.75 (d), 39.30 (t), 56.41 (d), 183.82; (D2O/DCl) 3.40 (t), 3.79 (t), 5.68 (d), 34.18 (t), 53.30 (d), 171.98
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