3-Furoic acid → 108206-23-1

4-piperidone hydrochloride monohydrate (0.32 g, 2.1 mmol) was dissolved in DCM (7 ml), and to this was added MP-Carbonate resin (0.8 g). This was stirred at room temperature for 2 h. Separately, 3-furoic acid (0.28 g, 2.52 mmol), N N-4-dimethylaminopyridine (cat.), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.2 g, 6.3 mmol) and TEA (0.25 ml) were dissolved in DCM (7 ml) and stirred at room temperature for 2 h. The 2 reaction mixtures were then combined and stirred at room temperature for 18 h. The resulting solution was then filtered and washed with HCl (1M), sodium bicarbonate then brine. The organic layers were combined and dried over MgSO4 and evaporated to dryness. The crude mixture was purified using flash chromatography (0-100% ethyl acetate in hexane), to yield a cream oil. 225 mg, (63%), LCMS tr=1.96 min (50% MeOH and 50% water at 0.5 ml/min), m/z M+H 194.16, HPLC tr=1.82 min (Isocratic 90% acetonitrile and 10% water at 1.0 ml/min), 100%, 1HNMR (CDCl3, 270 MHz) δ 2.41 (4H, t, J=6.2 Hz, CH2), 3.85 (4H, t, J=6.2 Hz, CH2), 6.50 (1H, dd, J=1.0, 2.0 Hz, ArH), 7.37 (1H, t, J=1.7 Hz, ArH), 7.68 (1H, dd, J=1.0, 1.7 Hz, ArH).

1. stirringstirred at room temperature for 2 h
2. customThe 2 reaction mixtures
3. stirringstirred at room temperature for 18 h
4. filtrationThe resulting solution was then filtered
5. washwashed with HCl (1M), sodium bicarbonate
6. dry with materialdried over MgSO4
7. customevaporated to dryness
8. customThe crude mixture was purified
9. customto yield a cream oil

ORD record

ord-f15578b376ca471682cbf3fb8b2d4b49

Source dataset

uspto-grants-2012_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08119627B2