HCID 11084286, compound → HCID 86755226, compound

Participants

Reaction Steps

(S)-(E,E)-N-Hexa-2,4-dienyl-α-methylbenzylamine (3) (0.500 g, 2.49 mmol), 1.6M butyllithium (1.35 ml, 2.16 mmol) and t-butyl sorbate (11) (0.279 g, 1.66 mmol) were reacted according the procedure of Example 1. Flash chromatography of the product on silica gel [ethyl acetate/petroleum ether (1:19)] afforded the title compound as a colourless oil (0.791 g, 72%). δH (200 MHz; CDCl3) 7.39-7.18 (5H, m, Ph), 6.12-5.93 (2H, m, CH=CH--CH=CH), 5.69-5.41 (4H, m, CH3CH=CH and CH=CH--CH=CH), 4.0 (1H, q, J=6.8, PhCHCH3), 3.87-3.75 (1H, m, CH3CH=CHCH), 3.21-3.09 (2H, m, NCH2), 2.40 (1H, dd, J=14.1 and 6.4, CH2CO2), 2.25 (1H, dd, J=14.1 and 8.5, CH2CO2), 1.76-1.71 (6H, m, CH3CH=CHCH and CH=CHCH3), 1.41 (9H, s, (CH3)3C), 1.37 (3H, d, J=6.7, PhCHCH3).

Provenance & Evidence