Gabapentin → Boc-Asp(OMe) Gabapentin

To a solution of Boc-Asp(OMe)-OH (5 g, 20 mmol) in acetonitrile (100 mL) was added N-hydroxysuccinimide (2.53 g, 22 mmol) and N,N-dicyclohexylcarbodiimide (4.5 g, 22 mmol). The reaction was stirred at ambient temperature for 4 h. The reaction mixture was filtered directly into an aqueous solution (100 mL) of gabapentin (3.77 g, 22 mmol) and sodium hydrogencarbonate (1.85 g, 22 mmol) and the resulting mixture stirred at ambient temperature for 16 h. The reaction was concentrated under reduced pressure, the residue dissolved in ethyl acetate/diethyl ether (1:1, 300 mL) and washed with 0.1M aqueous potassium hydrogensulfate (2×500 mL). The organic phase was separated, dried over Na2SO4, filtered, and concentrated to dryness under reduced pressure to afford Boc-Asp(OMe)-Gabapentin as a white solid (7.8 g, 19.5 mmol, 98%).

1. stirringthe resulting mixture stirred at ambient temperature for 16 h
2. concentrationThe reaction was concentrated under reduced pressure
3. dissolutionthe residue dissolved in ethyl acetate/diethyl ether (1:1, 300 mL)
4. washwashed with 0.1M aqueous potassium hydrogensulfate (2×500 mL)
5. customThe organic phase was separated
6. dry with materialdried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated to dryness under reduced pressure

ORD record

ord-a5352857d5b9435d9c482e161179277d

Source dataset

uspto-grants-2008_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07420002B2