(3S,alphaS)-t-Butyl 3-(alpha-methylbenzylamino)-3-phenylpropionate → (3R,alphaS)-t-Butyl 3-(alpha-methylbenzylamino)-4-hexenoate

Beteiligte Stoffe

Reaktionsschritte

The title compound (32) was prepared from compound (12) of Example 4 using the above-described procedure. [α]D21 -45.1 (c 1.69, CHCl3); νmax (CHCl3)/cm-1 1728 s (C=O); δH (300 MHz; CDCl3) 7.32-7.18 (5H, m, Ph), 5.55 (1H, dq, J=15.2 and 6.4, CH3CH=CH), 5.26 (ddq, J=15.2, 8.0 and 1.6, CH3CH=CH), 3.84 (1H, q, J=6.5, PhCHCH3), 3.45 (1H, m, NCHCH2), 2.41, 2.35 (2H, ABX system, JAB =14.5, JAX =6.6, JBX =6.5, CH2CO), 1.65 (3H, dd, J=6.4 and 1.6, CH3C=C), 1.45 (9H, s, (CH3)3C), 1.33 (3H, d, J=6.5, PhCHCH3); δC (50 MHz; CDCl3) 171.53 (C=O), 146.51 (Ph:Cipso), 133.07 (CH3C=C), 128.53, 126.82 (Ph:Cortho, Cmeta), 126.96 (Ph:Cpara), 80.28 (C(CH3)3), 55.14, 54.57 (CHN), 41.78 (CH2CO), 28.03 (C(CH3)3), 23.12 (NCHCH3), 17.83 (CH3C=C); m/z (CI) 290 (MH+, 100%), 234 (30), 174 (45), 105 (35); (Found: C, 74.61; H, 9.63; N, 4.62. C18H27NO2 requires C, 74.70; H, 9.40; N, 4.84%).

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