Synthesis and Structure Determination of (2S, 2′S)-3-Phenyl-2-(pyrrolidin-2′-yl)- propionic Acid

References

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• Compound 1: oil; yield: 70%. [α]D 20, −1.65 (c = 0.5, CHCl3). IR (cm−1, CHCl3): 1731, 1699. HRMS, Cacld. for C22H25NO4: 367.1784. Found: 367.1784. Compound 2: white powder; m.p. 94–95°C. [α]D 20, −1.45 (c = 0.5, CHCl3). IR (cm−1, CHCl3): 3062, 3031, 2973, 2887, 1700. Anal. Calcd. for C21H23NO4: C, 71.37; H, 6.56; N, 3.96. Found: C, 71.19; H, 6.49; N, 4.05. For both two compounds, the existence of rotator is observed in their NMR spectra
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• Compound 3: white powder, m.p. 248–249°C (Dec.).[α]D 20, −7.8 (c = 0.1, H2O). IR (cm−1, KBr): 3028, 2973, 2936, 1639, 1594. 1H NMR (δ, D2O, 400 MHz): 7.28–7.16 (m, 5H), 3.47–3.41 (m, 1H), 3.27–2.18 (m, 2H), 2.90–2.82 (m, 1H), 2.77–2.71 (m, 1H), 2.13–1.27 (m, 1H), 1.98–1.93 (m, 1H), 1.91–1.85 (m, 1H), 1.65–1.59 (m, 1H). 13C NMR (δ, D2O, 400 MHz): 177.57, 137.58, 127.60, 125.57, 60.45, 50.57, 44.34, 34.97, 26.65, 22.05. Anal. Calcd. for C13H17NO2: C, 71.21; H, 7.81; N, 6.39. Found: C, 70.87; H, 7.81; N, 6.45
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• Compound 4 : oil, yield, 63 %. [α]D 20, −3.0° (c = 0.2, EtOAc). IR (cm−1, CHCl3): 1703, 1698, 1693. 1H NMR (δ, CDCl3, 300 MHz): 7.50 (br, 1H), 7.29–7.18 (m, 5H), 3.57–3.53 (m, 1H), 3.45–3.38 (m, 2H), 3.28–3.24 (dd, 1H, J = 5.0, 14.5 Hz), 3.06–3.01 (dd, 1H, J = 6.1, 14.5 Hz), 2.64–2.58 (m, 1H), 2.03–1.94 (m, 2H), 1.87–1.69 (m, 1H), 1.40–1.34 (m, 1H). 13C NMR (δ, CDCl3, 400 MHz): 172.07, 150.55, 138.52, 129.68, 129.01, 127.21, 58.09, 48.49, 45.04, 33.12, 32.89, 23.65. HRMS, Cacld. for C14H16N2O2: 244.1212. Found: 244.1212
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• 2D H-H COSY (δ, CDCl3, 500 MHz): 3.49–3.48 (m, H-4a); 2.65–2.57 (m, H-4); 2.08–1.98 (m, 1H, H-5); 1.28–1.23 (m, 1H, H-5). 2D H-H NOESY (δ, CDCl3, 500 MHz): 2.08–1.98 (m, H-5a); 1.28–1.23 (m, H-5b). H-5a of 4 was differentiated from the two protons of 5-position by the observed NOE effects with H-4a. The other observed NOE effects between H-4 and H-5b supported the (4S, 4aS) configuration of 4
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