Acetic Anhydride → 2,4-Dioxo-3-(4-phenylbutyl)-3,9-diaza-bicyclo[3.3.1]nonane-9-carboxylic Acid Benzyl Ester

Participants

Reaction Steps

Anhydride 2 (0.54 g, 1.89 mmol, prepared from Compound 1) was dissolved in 1 mL of dioxane. 4-Phenylbutylamine (0.28 g, 1.89 mmol) was added from the top. The mixture was stirred at room temperature for 1 hour. After this time, acetic anhydride (0.62 mL, 3.78 mmol) was added, and the reaction was refluxed for 5 hours. The dioxane was evaporated, and flash chromatographic purification of the residue (40% EtOAc/hexanes) gave Compound 13 (0.75 g, 95% yield) as a colorless thick oil. Rf=0.66 (40% EtOAc/hexanes); IR: 2935, 2863, 1710, 1688, 1430, 1341, 1311, 1256, 1126, 1096, 1069, 749, 699 cm−1; 1H NMR: δ 1.41-2.04 (m, 8H), 2.61 (t, 2H, J=6.9), 3.79 (t, 2H, J=6.9), 4.96 (s, 2H), 5.14 (s, 2H), 7.14-7.37 (m, 10H).

Provenance & Evidence