Hydrogen Peroxide → HCID 67328822, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution containing 114 mg (0.26 mmol) of 5-Bromo-4-methoxy-6-(10-(methoxymethoxy)decyl)-N,N-dimethylpyridin-2-amine in 5 mL of anhydrous THF were added 413 μL (0.66 mmol) of 1.6M n-BuLi in pentane. The reaction mixture was stirred at 23° C. for 10 minutes. Then, were added 89.0 μL (0.79 mmol) of trymethyl borate and the mixture was stirred at 23° C. for 30 minutes. Then, were added 684 μL (12.6 mmol) of 35% aq H2O2 followed by 684 μL of 1N NaOH. The reaction mixture was stirred at 23° C. for 2 h and then poured into 20 mL of water. The mixture was extracted with two 20-mL portions of ethyl acetate. The combined organic layer was washed with one 20-mL portion of brine, dried (MgSO4) and concentrated under diminished pressure. The residue was purified by chromatography on a silica gel column (2×10 cm). Elution with 1:1 hexanes-ethyl acetate afforded the expected product as a yellowish oil: yield 20 mg (21%); silica gel TLC Rf 0.1 (1:1 hexanes-ethyl acetate); 1H NMR (methanol) δ 1.29 (br s, 12H), 1.56 (br m, 4H), 2.66 (dd, 2H, J=7.6, 7.6 Hz), 3.00 (s, 6H), 3.29 (s, 3H), 3.48 (t, 2H, J=6.8 Hz), 3.90 (s, 3H), 4.56 (s, 2H) and 6.11 (s, 1H); 13C NMR (methanol-d4) δ 25.85, 28.06, 29.07, 29.11, 29.19, 29.24, 29.37, 30.10, 35.20, 38.17, 38.17, 53.94, 54.93, 67.46, 87.91, 95.98, 132.79, 143.67, 153.94 and 157.39; mass spectrum (APCI), m/z (M+H)+369.2760 (C20H37N2O4 requires 369.2753)

Provenance & Evidence