t-Butyl 4-phenyl-2-butenoate → (3R,alphaS)-t-Butyl 3-(alpha-methylbenzylamino)-4-methylpentanoate

Participants

Reaction Steps

The title compound (34) was prepared from compound (16) of Example 6 using the above-described procedure. [α]D21 -52.7 (c 1.57, CHCl3); νmax (CHCl3)/cm-1 1724 s (C=O); δH (300 Hz; CDCl3) 7.38-7.21 (5H, m, Ph), 3.88 (1H, q, J=6.5, PhCHCH3), 2.60 (1H, m, NCHCH2), 2.38, 2.27 (2H, ABX system, JAB =14.4, JAX =5.4, JBX =6.2, CH2CO), 1.68 (1H, m, (CH3)2CH), 1.47 (9H, s, (CH3)3C), 1.33) (3H, d, J=6.5, PhCHCH3), 0.89 (3H, d, J=6.8, (CH3)2CH), 0.81 (3H, d, J=6.8, (CH3)2CH); δC (50 MHz; CDCl3) 172.67 (C=O), 146.58 (Ph:Cipso), 128.42, 127.12 (Ph:Cortho, Cmeta), 126.95 (Ph:Cpara), 80.19 (C(CH3)3), 57.82, 55.37 (CHN), 36.81 (CH2CO), 31.14 ((CH3)2CH), 28.03 (C(CH3)3), 24.76 (NCHCH3), 18.78, 18.32 ((CH3)2CH); m/z (CI) 292 (MH+, 100%), 236 (20), 192 (20), 176 (17), 105 (20); (Found: C, 74.07; H, 10.31; N, 4.58. C18H29NO2 requires C, 74.18; H, 10.03; N, 4.81%).

Provenance & Evidence