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

Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
icon
Related questions
Question
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
Expert Solution
trending now

Trending now

This is a popular solution!

steps

Step by step

Solved in 2 steps with 2 images

Blurred answer
Similar questions
Recommended textbooks for you
Chemistry
Chemistry
Chemistry
ISBN:
9781305957404
Author:
Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:
Cengage Learning
Chemistry
Chemistry
Chemistry
ISBN:
9781259911156
Author:
Raymond Chang Dr., Jason Overby Professor
Publisher:
McGraw-Hill Education
Principles of Instrumental Analysis
Principles of Instrumental Analysis
Chemistry
ISBN:
9781305577213
Author:
Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:
Cengage Learning
Organic Chemistry
Organic Chemistry
Chemistry
ISBN:
9780078021558
Author:
Janice Gorzynski Smith Dr.
Publisher:
McGraw-Hill Education
Chemistry: Principles and Reactions
Chemistry: Principles and Reactions
Chemistry
ISBN:
9781305079373
Author:
William L. Masterton, Cecile N. Hurley
Publisher:
Cengage Learning
Elementary Principles of Chemical Processes, Bind…
Elementary Principles of Chemical Processes, Bind…
Chemistry
ISBN:
9781118431221
Author:
Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:
WILEY