Gabapentin → 2-[({[(2-Methylpropanoyloxy)ethoxy]carbonylamino}methyl)cyclohexyl]acetic Acid

A 50 mL, single-neck, round-bottomed flask equipped with a magnetic stir bar and a nitrogen inlet was charged with sulfone D3 (300 mg, 1 mmol) and gabapentin (171 mg, 1 mmol) in acetonitrile (1 mL). To the resulting slurry, saturated aqueous potassium bicarbonate (1 mL) was slowly added over a period of two minutes. The reaction mixture was stirred overnight at room temperature. The reaction mixture was then poured into a separatory funnel, diluted with diethyl ether (20 mL), washed with 5% aqueous sulfuric acid (10 mL), water (10 mL), and brine (100 mL). The organic phase was dried over sodium sulfate and evaporated under vacuum to give a viscous oil. The crude product was purified by column chromatography using ethyl acetate and hexane to give the title compound E4 as a viscous oil (250 mg, 75% yield). 1H NMR (CDCl3, 400 MHz): δ 1.16 (d, J=6.8 Hz, 6H), 1.35-1.55 (m, 10H), 1.46 (d, J=5.2 Hz, 3H), 2.32 (s, 2H), 2.52 (m, 1H), 3.23 (d, J=6.8 Hz, 2H), 5.27 (t, J=6.4 Hz, 1H, —NH) 6.76 (q, J=5.6 Hz, 1H).

1. customA 50 mL, single-neck, round-bottomed flask equipped with a magnetic stir bar and a nitrogen inlet
2. additionThe reaction mixture was then poured into a separatory funnel
3. washwashed with 5% aqueous sulfuric acid (10 mL), water (10 mL), and brine (100 mL)
4. dry with materialThe organic phase was dried over sodium sulfate
5. customevaporated under vacuum
6. customto give a viscous oil
7. customThe crude product was purified by column chromatography

ORD record

ord-614c1eaef788409cb7c8d5fa4f4e20b2

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08299291B2