Gabapentin → 1-[[[(1-Chlorobutoxy)carbonyl]amino]methyl]cyclohexaneacetic acid
Reaction equation
[CH2:1]1[CH2:6][CH2:5][C:4]([CH2:11][NH2:12])([CH2:7][C:8]([OH:10])=[O:9])[CH2:3][CH2:2]1.C(N([CH2:18][CH3:19])CC)C.[CH3:20][Si](Cl)(C)C.Cl[C:26]([O-:28])=[O:27].Cl[CH2:30][Cl:31]>>[Cl:31][CH:30]([O:28][C:26]([NH:12][CH2:11][C:4]1([CH2:7][C:8]([OH:10])=[O:9])[CH2:3][CH2:2][CH2:1][CH2:6][CH2:5]1)=[O:27])[CH2:20][CH2:18][CH3:19]Participants
6
Conditions
- Temperature
- 0 °C
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.
Workup
- stirringThe reaction was stirred for another hour at room temperature
- customquenched with citric acid
- extractionextracted with dichloromethane
- washThe combined organic phase was washed with water and brine
- dry with materialdried over Na2SO4
- filtrationFiltration and evaporation
Sources & evidence
- ORD record
- ord-db2699372fff468f8b2537b39b6a524d
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08168623B2
Reaction notes
Loading…