Compound 96
ethyl (S)-2-acetamido-3-(4-(piperidin-1-yl)phenyl)propanoate
From: Practical and regioselective amination of arenes using alkyl amines
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Compound data: NMR
Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.
Following GP2 outlined for compound 45, in 1,1,1,3,3,3-hexafluoro-i-propanol (HFIP) at 0 °C, azetidine hydrochloride (10 mg, 0.1 mmol), ethyl L-acetylphenylalaninate (47 mg, 0.2 mmol) and 6.0 equiv. of HClO4 gave 96 and 96* (24 mg, 65%) as an wax. p:m 6:1. Rf 0.19 [CHCl3–EtOH (95:5)]; FT-IR νmax (film)/cm–1, 2921, 2868, 2096, 1711, 1234, 1080; 1H NMR (CDCl3, 500 MHz); 1H NMR (500 MHz, CDCl3) δ 6.98 (2H, d, J = 8.5 Hz), 6.84 (2H, d, J = 8.5 Hz), 5.88 (1H, d, J = 7.7 Hz), 4.81 (1H, dt, J = 7.7, 5.7 Hz), 4.17 (2H, q, J = 7.1 Hz), 3.56 (1H, tt, J = 8.9, 3.9 Hz), 3.51 (2H, dt, J = 12.7, 4.4 Hz), 3.05 (2H, ABq, JAB = 15.4, 5.6, 2.7 Hz), 2.92 (2H, ddd, J=12.5, 9.8, 2.9 Hz), 2.06 – 2.00 (2H, m), 1.98 (3H, s), 1.77 (2H, dp, J = 14.3, 5.5, 4.6 Hz), 1.26 (3H, t, J = 7.1 Hz); 13C NMR (126 MHz, CDCl3) δ 171.9, 169.7, 150.2, 130.2, 127.0, 116.8, 61.6, 57.7, 53.3, 47.7, 37.1, 30.7, 23.4, 14.3; HRMS (ASAP POS): Found MH+ 360.2033, C18H26N5O3 requires 360.2030.
