Water → HCID 68491840, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 239 (970 mg, 4.4 mmol) in acetone (10 ml) was added potassium C(Ar)bonate (3.06 g, 22.0 mmol), benzyl bromide (1.05 ml, 8.8 mmol) and tetrabutyl ammonium iodide (163 mg, 0.44 mmol). The reaction mixture was heated at 55° C. for 60 h. The reaction mixture was cooled to rt, water (20 ml) was added and the aqueous layer was extracted with ethyl acetate (3×30 ml). The combined organic phases were dried (MgSO4) and concentrated in vacuo. Purification by flash column chromatography eluting with EtOAc then EtOAc:MeOH:TEA; 10:1:0.1 afforded the title compound (882 mg, 64%) as a pale orange solid. mp=87.9-90° C. 1H NMR (270 MHz; CDCl3) 1.16 (6H, s, 2×CH3), 2.22 (3H, s, CH3), 2.59 (2H, s, CH2), 3.90 (3H, s, OCH3), 5.13 (2H, s, CH2Ph), 6.63 (1H, s, CH), 7.0 (1H, s, CH), 7.27-7.46 (5H, m, 5×CH, phenyl). 13C NMR (67.5 MHz; CDCl3) 23.54 (CH3), 28.15 (2×CH3), 38.70 (CH2), 53.65 (C(CH3)), 56.07 (OCH3), 71.87 (CH2Ph), 111.40 (CH), 112.57 (CH), 121.49 (C), 127.58 (CH), 128.08 (CH), 128.68 (CH), 130.78 (C), 137.15 (C), 146.33 (C), 151.79 (C), 160.65 (C). LC/MS (ES+) tr=2.5 min, m/z 310.05 (M++H). HRMS (ES+) calcd. for C20H24NO2 (M++H) 310.1802, found 310.1801.

Provenance & Evidence