Reaction #1000391

Reaction equation

gabapentin

[(1-isobutanoyloxyethoxy)carbonyloxy]succinimide

→

title compound

Yield 101.2%

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

Yield 101.2%

Solvents

water

acetonitrile

methyl tert-butyl ether

Conditions

Workup

1. 1
   Washwashed with water (2×100 mL) and brine (50 mL)
2. 2
   OtherThe organic phase is separated
3. 3
   Dryingdried over anhydrous sodium sulfate
4. 4
   Filtrationfiltered
5. 5
   Concentrationconcentrated in vacuo

Procedure

To a solution of gabapentin (6.8 g, 0.04 mole) in water (40 mL) is added a solution of [(1-isobutanoyloxyethoxy)carbonyloxy]succinimide (10 g, 0.036 mol) in acetonitrile (40 mL) over a period of 30 minutes. The reaction is stirred at ambient temperature for 3 hours. The reaction mixture is diluted with methyl tert-butyl ether (200 mL), washed with water (2×100 mL) and brine (50 mL). The organic phase is separated, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to afford the title compound as a white solid (12 g, quantitative).

Source