N-Iodosuccinimide → HCID 86755238, compound

Participants

Reaction Steps

Compound (28) from Example 13 (0.200 g, 0.44 mmol) was treated with N-iodosuccinimide (0.197 g, 0.88 mmol) using standard iodoetherification conditions. Flash chromatography of the product on silica gel [ethyl acetate/petroleum (1:9)] afforded the title compound (54) (Rf 0.50) as a yellow oil (0.093 g, 45%). δH (200 MHz; CDCl3) 7.72 (1H, d, J=16.0, CH=CHPh), 7.57-7.22 (15H, m, Ph), 6.51 (1H, d, J=16.0, PhCH=CH), 5.45 (1H, d, J=4.9, CHCHOH), 4.25 (1H, d, J=4.9, PhCHCH), 3.81 (1H, d, J=6.5, PhCHCH3), 1.92 (1H, br s, OH), 1.34 (3H, d, J=6.5, PhCHCH3), 1.32 (9H, s, (CH3)3C). The corresponding 3-(α-methylbenzylamino) derivative (Rf 0.25) was also recovered as a colourless oil (0.045 g, 30%. δH (200 MHz; CDCl3) 7.48-7.14 (10H, m, Ph), 4.50 (1H, d, J=3.8, CHCHOH), 4.09 (1H, d, J=3.8, PhCHCH), 3.76 (1H, q, J=6.6, PhCHCH3), 1.38 (3H, d, J=6.6, PhCHCH3), 1.31 (9H, s, (CH3)3C).

Provenance & Evidence