Reaction #476541

Reaction equation

gabapentin

sodium bicarbonate

compound ( 10 )

[(1-Isobutanoyloxyethoxy)carbonyloxy]Succinimide

→

title compound ( 12 )

Yield 96.0%

{[(1-Isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-Cyclohexane Acetic Acid

Yield 96.0%

Solvents

diethyl ether

water

acetonitrile

Conditions

Workup

1. 1
   Washwashed with 0.1 M aqueous potassium bisulfate (3×100 mL)
2. 2
   OtherThe organic phase was separated
3. 3
   Dryingdried over anhydrous magnesium sulfate
4. 4
   Filtrationfiltered
5. 5
   Concentrationconcentrated in vacuo

Procedure

To a solution of gabapentin (1.7 g, 10 mmol) and sodium bicarbonate (20 mmol) in water (40 mL) was added a solution of compound (10) (2.73 g, 10 mmol) in acetonitrile (20 mL) over 1 min. The reaction was stirred at ambient temperature for 16 h. The reaction mixture was diluted with diethyl ether (100 mL) and washed with 0.1 M aqueous potassium bisulfate (3×100 mL). The organic phase was separated, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to afford the title compound (12) as a white solid (2.7 g, 96%). The product was recrystallized by dissolution in 1:10 ethyl acetate:heptane (10 mL) at 60° C., followed by slow cooling to 4° C. The white crystalline product was isolated by filtration. Melting point: 63-64° C. 1H NMR (CDCl3, 400 MHz): 1.15 (d, 6H), 1.40-1.55 (m, 10H), 1.45 (d, 3H), 2.32 (s, 2H), 2.49-2.56 (m, 1H), 3.23 (d, 2H), 5.41 (t, 1H), 6.75 (q, 1H). MS (ESI) m/z 330.29 (M+H+).

Source