Reaction #544481

Reaction equation

triethylamine

TMSCl

gabapentin

chloroformate

1-Chlorobutyl-1-chloroformate

→

crude product ( 133 )

Yield 62.1%

[(α-Chlorobutoxy)carbonyl]aminomethyl-1-Cyclohexane Acetic Acid

Yield 62.1%

Solvents

dichloromethane

dichloromethane

Conditions

Workup

1. 1
   workup.STIRRINGThe reaction was stirred for another hour at room temperature
2. 2
   Otherquenched with citric acid
3. 3
   Extractionextracted with dichloromethane
4. 4
   WashThe combined organic phase was washed with water and brine
5. 5
   Dryingdried over Na2SO4
6. 6
   FiltrationFiltration and evaporation

Procedure

To a suspension of gabapentin (8.55 g, 50 mmol) in dichloromethane at 0° C. was added triethylamine (21 mL, 150 mmol) and TMSCl (6.4 mL, 50 mmol). The resulting suspension was stirred at 0° C. for 20 minutes and then a solution of chloroformate (132) (8.55 g, 50 mmol) in dichloromethane was added. The reaction was stirred for another hour at room temperature, then quenched with citric acid and extracted with dichloromethane. The combined organic phase was washed with water and brine and dried over Na2SO4. Filtration and evaporation gave 9.5 g of crude product (133), which was used directly in the subsequent step.

Source