Benzoic Acid → (+/-)-(4-Isopropylphenyl){1-[4-(trifluoromethyl)phenyl]but-3-en-1-yl}amine

Participants

Reaction Steps

Lanthanum triflate (0.141 g, 0.24 mmol, 2 mol %) and benzoic acid (1.49 g, 12.2 mmol) were dissolved in CH3CN (20 ml) and the suspension was stirred under nitrogen until dissolved. 4-(Trifluoromethyl)benzaldehyde (2.12 g, 12.2 mmol) was added followed by 4-isopropylaniline (1.65 g). Allyl(tributyl)stannane (4.54 ml, 14.6 mmol) was then added and the mixture was stirred at room temperature overnight. The mixture was then quenched with NaOH (2M, 20 ml) and extracted into DCM (3×100 ml). The combined extracts were dried (MgSO4) and the solvent was removed in vacuo to yield the crude homoallylic amine product. This was purified by chromatography on silica using 10-30% ether in hexane as eluant to yield the product as a colourless oil (3.65 g, 90%). 1H NMR (500 MHz, CDCl3) δ: 1.16 (6H, dd, J 1.3, 6.9), 2.42-2.48 (1H, m), 2.56-2.62 (1H, m), 2.71-2.79 (1H, qn, J 6.7), 4.07 (1H, s), 4.38 (1H, dd, J 4.9, 8.1), 5.18 (2H, m), 5.69-5.77 (1H, m), 6.40 (2H, d, J 8.4), 6.95 (2H, d, J 8.5), 7.49 (2H, d, J 8.1), 7.57 (2H, d, J 8.1); M/Z (ES+) 334 (MH+).

Provenance & Evidence