Of the early antihistamines, most had a side effect of mild sedation; they made a person sleepy. More recently, a new generation of nonsedating antihistamines known as hista- mine H, receptor antagonists has been introduced. One of the most widely prescribed of these is fexofenadine (Allegra). This compound is nonsedating because the polarity of its carboxylic anion prevents it from crossing the blood-brain barrier. Following is a retrosynthetic analysis for the synthesis of fexofenadine. COOH HO Fexofenadine (Allegra) go H. COO НО (H) (C) NH Br COOH Br HO 4-Bromobutanal (В) (G) CN (F) Br (4-Bromophenyl)ethanenitrile (A) Br NH OEt Bromo- Ethyl 4-piperidine- carboxylate (E) benzene (D) (Note: The organolithium reagent C cannot be made directly from B because the pres- ence of the carboxyl group in B would lead to intermolecular destruction of the reagent by an acid-base reaction. In practice, B is first converted to its sodium salt by treatment with sodium hydride, NaH, and then the organolithium reagent is prepared.)

Of the early antihistamines, most had a side effect of mild sedation; they made a person sleepy. More recently, a new generation of nonsedating antihistamines known as hista- mine H, receptor antagonists has been introduced. One of the most widely prescribed of these is fexofenadine (Allegra). This compound is nonsedating because the polarity of its carboxylic anion prevents it from crossing the blood-brain barrier. Following is a retrosynthetic analysis for the synthesis of fexofenadine. COOH HO Fexofenadine (Allegra) go H. COO НО (H) (C) NH Br COOH Br HO 4-Bromobutanal (В) (G) CN (F) Br (4-Bromophenyl)ethanenitrile (A) Br NH OEt Bromo- Ethyl 4-piperidine- carboxylate (E) benzene (D) (Note: The organolithium reagent C cannot be made directly from B because the pres- ence of the carboxyl group in B would lead to intermolecular destruction of the reagent by an acid-base reaction. In practice, B is first converted to its sodium salt by treatment with sodium hydride, NaH, and then the organolithium reagent is prepared.)

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter23: Amines

Section: Chapter Questions

Problem 23.71P

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