Water → HCID 68492920, compound

Participants

Reaction Conditions

Reaction Steps

A solution of B1 (345 mg, 1.5 mmol), and 2-methoxybenzyl chloride (230 μL, 1.65 mmol) in DMF (10 mL) was treated with Huning's base (1.82 mL, 10.5 mmol) and heated to 80° C. for 60 h. After cooling to room temperature, water (5 mL) was added and the product extracted with ethyl acetate (4×10 mL). The combined organics were washed with water, brine and dried over MgSO4, prior to evaporation and purification by flash column chromatography. B16 was isolated as a white solid in 85% yield (345 mg). m.p. 148-155° C.; Rf: 0.23 (1:1 Petrol:ethyl acetate) 1H NMR (270 MHz, CDCl3) δ 2.66-2.70 (2H, m), 2.73-2.76 (2H, m), 3.59 (2H, br s), 3.74 (2H, br s), 3.75 (3H, s), 6.20 (1H, d, J=2.43), 6.39 (1H, dd, J=2.7, 9.2), 6.73 (1H, d, J=9.2) 6.83-6.92 (2H, m), 7.24 (1H, dt, J=1.6, 8.1), 7.36 (1H, dd, J=1.4, 8.1); HRMS (ES+) calcd. for C17H20NO2 (M++H) 270.1489, found 270.1478; LC/MS (ES+) tr=1.92 min, m/z 270.4 (M++H); HPLC tr=2.917 min (>98%).

Provenance & Evidence