Succinic anhydride → HCID 58482718, compound

Participants

Reaction Steps

Benzyl 4-hydroxy-1-piperidinecarboxylate (1.0 g, 4.25 mmol), succinic anhydride (0.425 g, 4.25 mmol) and 4-DMAP (52 mg, 0.425 mmol) were dissolved in CHCl3 (10 mL) and stirred for 24 hours. The volatiles were removed in vacuo. Aqueous NaHCO3 (100 mL) was added and the mixture was washed with Et2O (2×50 mL). The aqueous layer was acidified to pH=6 to 7 with 2N HCl and extracted with CH2Cl2 (2×60 mL). The combined organic extracts were washed with brine (60 mL), dried over Na2SO4 and concentrated in vacuo to afford compound 64 (768 mg, 54%) which was used without further purification. 1H NMR (400 MHz, CDCl3) δ 1.62 (m, 2H), 1.85 (m, 2H), 2.60-2.70 (m, 4H), 3.38 (m, 2H), 3.74 (m, 2H), 4.97 (m, 1H), 5.12 (s, 2H), 7.35 (m, 5H).

Provenance & Evidence