Tert-butyl cinnamate → (3R,alphaS)-t-Butyl 3-(N-cinnamyl-alpha-methylbenzylamino)-3-phenylpropionate

Participants

Reaction Steps

(S)-N-cinnamyl-α-methylbenzylamine (4) (0.100 g, 0.42 mmol), 1.6M butyllithium (0.242 ml, 0.39 mmol) and t-butyl cinnamate (7) (0.072 g, 0.35 mmol) were reacted according to the procedure of Example 1. Flash chromatography of the product on silica gel [ethyl acetate/petroleum ether (1:49)] afforded the title compound (Rf 0.3) as a colourless oil (0.145 g, 78%). δH (300 MHz; CDCl3) 7.50-7.18 (15H, m, Ph), 6.42 (1H, d, J=16.0, PhCH=CH), 6.11 (1H, dt, J=16.0 and 6.2; CH=CHPh), 4.53 (1H, dd, J=8.7 and 6.4, PhCHCH2), 4.07 (1H, q, J=6.7, PhCHCH3), 3.32 (2H, dd, J=6.2 and 1.1, NCH2), 2.83 (1H, dd, J=14.6 and 6.4, CH2CO2), 2.62 (1H, dd, J=14.6 and 8.7, CH2CO2), 1.31 (9H, s, (CH3)3C), 1.27 (3H, d, J=6.7, PhCHCH3).

Provenance & Evidence