Acetic Anhydride → HCID 86650693, compound

Participants

Reaction Steps

A stirred solution of ethyl 3-oxo-3-(2,3,4,5-tetrafluorophenyl)propionate (2.80 g, 10.6 mmol), Ac2O (6.01 mL, 63.6 mmol) and triethyl orthoformate (3.53 mL, 21.2 mmol) was heated at 120° C. for 3 hours. The mixture was concentrated in vacuo and dried under high vacuum. The crude product was dissolved in toluene (30 mL) and a suspension of [1-(aminomethyl)cyclobutyl]]methanol hydrochloride (1.60 g, 10.6 mmol) in toluene (20 mL) and triethylamine (1.48 mL, 10.6 mmol) were added under ice-cooling. The mixture was stirred at room temperature for 6 hours and concentrated in vacuo to yield the crude product. The crude product was purified by column chromatography (Hexane: EtOAc 10:1→2:1) to yield the title compound (1.88 g, 46%) as a white solid. 1H-NMR (400 MHz, CDCl3) δ 0.95-1.12 (3H, m), 1.66-1.69 (1H, m), 1.81-1.91 (4H, m), 1.94-2.03 (2H, m), 3.57 (2H, d, J=6.7 Hz), 3.72 (2H, d, J=4.3 Hz), 4.00-4.10 (2H, m), 6.96-7.12 (1H, m), 8.09-8.15 (1H, m), 9.65-11.15 (1H, m).

Provenance & Evidence