Gabapentin, an anticonvulsant used in the treatment of epilepsy, is structurally related to the neurotransmitter 4-aminobutanoic acid (GABA). -NH2 -NH, B -СООН COOH Gabapentin 4-Aminobutanoic acid (y-Aminobutyric acid, GABA) Gabapentin was designed specifically to be more lipophilic than GABA and therefore more likely to cross the blood-brain barrier, the lipidlike protective membrane that sur- rounds the capillary system in the brain and prevents hydrophilic (water-loving) com- pounds from entering the brain by passive diffusion. Given the following retrosynthetic analysis, propose a synthesis for gabapentin. -NH, -NH2 CN COOH -COOEt COOEt Gabapentin COOEt COOE. O + COOEt COOEt Cyclohexanone Diethyl malonate

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Gabapentin, an anticonvulsant used in the treatment of epilepsy, is structurally related
to the neurotransmitter 4-aminobutanoic acid (GABA).
-NH2
-NH,
B
-СООН
COOH
Gabapentin
4-Aminobutanoic acid
(y-Aminobutyric acid, GABA)
Gabapentin was designed specifically to be more lipophilic than GABA and therefore
more likely to cross the blood-brain barrier, the lipidlike protective membrane that sur-
rounds the capillary system in the brain and prevents hydrophilic (water-loving) com-
pounds from entering the brain by passive diffusion. Given the following retrosynthetic
analysis, propose a synthesis for gabapentin.
-NH,
-NH2
CN
COOH
-COOEt
COOEt
Gabapentin
COOEt
COOE.
O +
COOEt
COOEt
Cyclohexanone
Diethyl
malonate
Transcribed Image Text:Gabapentin, an anticonvulsant used in the treatment of epilepsy, is structurally related to the neurotransmitter 4-aminobutanoic acid (GABA). -NH2 -NH, B -СООН COOH Gabapentin 4-Aminobutanoic acid (y-Aminobutyric acid, GABA) Gabapentin was designed specifically to be more lipophilic than GABA and therefore more likely to cross the blood-brain barrier, the lipidlike protective membrane that sur- rounds the capillary system in the brain and prevents hydrophilic (water-loving) com- pounds from entering the brain by passive diffusion. Given the following retrosynthetic analysis, propose a synthesis for gabapentin. -NH, -NH2 CN COOH -COOEt COOEt Gabapentin COOEt COOE. O + COOEt COOEt Cyclohexanone Diethyl malonate
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