Reaction Steps
A mixture of 225 (300 mg, 0.83 mmol), 3-methoxybenzyl chloride (0.13 ml, 0.91 mmol) and TEA (0.3 ml, 1.65 mmol) in EtOH (3 ml) was heated in the microwave at 130° C. for 1.5 h. The reaction mixture was concentrated in vacuo. The crude residue was dissolved in EtOAc (30 ml), washed with brine (20 ml), dried (MgSO4) and concentrated in vacuo. Purification (flashmaster: 20 g, 100% hex to 50% hex/50% EtOAc and then to 100% EtOAc) afforded the title compound (246 mg, 62%) as colourless oil. 1H NMR (270 MHz; CDCl3) 1.04 (18H, d, J=6.7 Hz, CH3CH), 1.12-1.22 (3H, m, 3×SiCHCH3), 1.17 (6H, s, 2×CH3), 2.65 (2H, s, CH2), 3.47 (2H, s, CH2), 3.64 (2H, s, CH2), 3.74 (3H, s, OCH3), 3.79 (3H, s, OCH3), 6.41 (1H, s, CH), 6.48 (1H, s, CH), 6.77 (1H, ddd, J=8.2, 2.2, 1.2 Hz, CH), 6.95-6.98 (2H, m, 2×CH), 7.22 (1H, t, J=8.2 Hz, CH). 13C NMR (67.5 MHz; CDCl3) 12.38 (CH), 17.49 (CH3), 23.26 (CH3), 42.28 (CH2), 49.64 (CH2), 52.11 (C), 53.22 (CH2), 54.72 (OCH3), 55.04 (OCH3), 111.42 (CH), 111.69 (CH), 113.77 (CH), 117.21 (CH), 120.56 (CH), 125.68 (C), 126.34 (C), 128.69 (CH), 142.09 (C), 142.89 (C), 148.66 (C), 159.15 (C). LC/MS (ES+) tr=4.54 min, m/z 484.83 (M++H). HRMS (ES+) calcd. for C29H46NO3Si (M++H) 484.3241, found 484.3242.
