Reaction Steps
A solution of 213 (300 mg, 1.1 mmol), TEA (0.3 ml, 2.1 mmol) and 3-methoxybenzyl chloride (0.18 ml, 1.3 mmol) in EtOH (3 ml) was heated in the microwave at 130° C. for 1.5 h. The reaction mixture was concentrated in vacuo and the crude residue was dissolved in EtOAc (30 ml) and washed with brine (30 ml). The organic layer was dried (MgSO4) and concentrated in vacuo. Purification (flashmaster: 20 g, 100% hex to 100% EtOAc over 25 min) afforded the title compound (357 mg, 84%) as a colourless oil. 1H NMR (270 MHz; CDCl3) 1.12 (3H, d, J=6.4 Hz, CH3CH), 2.47 (1H, dd, J=16.1, 5.7 Hz, CHH), 2.86 (1H, dd, J=16.1, 4.9 Hz, CHH), 3.0-3.11 (1H, m, CH3CH), 3.55 (2H, t, J=13.4 Hz, CH2), 3.76-3.81 (2H, m, CH2), 3.80 (6H, s, 2×OCH3), 5.10 (2H, s, CH2Ph), 6.47 (1H, s, CH), 6.60 (1H, s, CH), 6.79 (1H, ddd, J=8.2, 2.5, 1.0 Hz, CH), 6.94-6.97 (2H, m, 2×CH), 7.15-7.45 (6H, m, 5×CH, phenyl and CH). 13C (67.5 MHz; CDCl3) 15.31 (CH3), 35.03 (CH2), 51.51 (CH2), 52.27 (CH), 55.32 (CH3), 56.11 (CH3), 57.24 (CH2), 71.21 (CH2), 109.95 (CH), 112.48 (CH), 114.36 (CH), 114.56 (CH), 121.32 (CH),125.83 (C), 126.95 (C), 127.37 (CH), 127.82 (CH), 128.59 (CH), 129.30 (CH), 137.47 (C), 141.35 (C), 146.73 (C), 147.91 (C), 159.77 (C). LC/MS (ES+) tr=1.52 min, m/z 404.25 (M++H).
