Oxazolinium salts and method of preparation

Details Oxazolinium salts and method of preparation Oxazolinium salts and method of preparation

1978-10-26

1980-12-02

Sutto, Anton H.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

2605706, C07D26312, C07D26314

Patent

active

042373042

ABSTRACT:
1-Aryl-1-hydroxy-2-methylaminopropanes are rearranged from the erythro isomer to the threo isomer by the process of (1) forming the O,N-diacyl derivative of the arylpropanolamine; (2) reacting the product of step (1) with an anhydrous or substantially anhydrous protic acid (thereby forming a novel oxazolinium salt); and (3) reacting the oxazolinium salt from step (2) with an aqueous protic acid. The threo isomer of the arylpropanolamine is thus produced as an amine/acid salt. This salt can be further purified, if desired, by neutralizing the acid/amine salt with caustic isolating the free amine and reprotonating the free base in isopropanol with, for example, anhydrous HCl. This process is particularly applicable to manufacture of d-pseudoephedrine from 1-ephedrine.

REFERENCES:
patent: 2513346 (1950-07-01), Moersch et al.
patent: 2530627 (1950-11-01), Pfister et al.
patent: 2564423 (1951-08-01), Barnum
patent: 2714082 (1955-07-01), Davies et al.
patent: 3278544 (1966-10-01), Easton
patent: 4024184 (1977-05-01), Kaiser et al.

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