Following is an outline for a synthesis of the anorexic
Chapter 23, Problem 23.64(choose chapter or problem)
Following is an outline for a synthesis of the anorexic (appetite suppressant) fenfl uramine. This compound was one of the two ingredients in Phen-Fen, a weight-loss preparation now banned because of its potential to cause irreversible heart valve damage. CF3 CF3 O CF3 N9OH NH2 CF3 H N O CF3 H N CF3 Fenfluramine 1 2 3 4 5 (a) Propose reagents and conditions for Step 1. Account for the fact that the CF3 group is meta directing. (b) Propose reagents and experimental conditions for Steps 2 and 3. (c) An alternative procedure for preparing the amine of Step 3 is reductive amination of the corresponding ketone. What is reductive amination? Why might this two-step route for formation of the amine be preferred over the one-step reductive amination? (d) Propose reagents for Steps 4 and 5. (e) Is fenfl uramine chiral? If so, which of the possible stereoisomers are formed in this synthesis?
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