New route to phenylephrine

✍ Scribed by Peter B. Russell; Scott J. Childress

• Publisher: John Wiley and Sons
• Year: 1961
• Tongue: English
• Weight: 98 KB
• Volume: 50
• Category: Article
• ISSN: 0022-3549
• DOI: 10.1002/jps.2600500824

✦ Synopsis

Lithium aluminum hydride reduction of 3benzyloxy-N-methylmandelamide followed by debenzylation has afforded phenylephrine.

HE REACTION of an a-haloketone with a primary T aliphatic amine is one that can give rise to considerable tar formation (1). Although this reaction is successfully used commercially in the manufacture of phenylephrine (3-hydroxy-a-methylaminomethylbenzyl alcohol), it is not entirely satisfactory, As a means of avoiding this step in the preparation of phenylephrine, we have developed the following route, each step of which proceeds in good yield and without tar formation.