Mabuterol Synthesis
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Mabuterol is a selective β2 adrenoreceptor agonist.


Synthesis

The halogenation of 2-(Trifluoromethyl)aniline 8-17-5(1) with iodine and sodium bicarbonate resulted in 2-Amino-5-Iodobenzotrifluoride
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(2). Protection with acetic anhydride followed by nucleophilic aromatic displacement with copper(I)cyanide gave N- -cyano-2-(trifluoromethyl)phenylcetamide
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(3). Hydrolysis of the nitrile and the protecting group gave 4-amino-3-(trifluoromethyl)benzoic acid 00-76-0(4). Halogenation with chlorine gave 4-Amino-3-Chloro-5-(Trifluoromethyl)Benzoic Acid 5656-52-3(5). Halogenation of the acid with thionyl chloride gave 4-Amino-3-chloro-5-(trifluoromethyl)benzoylchloride 3498-15-7(6). Treatment with diethyl malonate 05-53-3gave the acetophenone and hence 1- -amino-3-chloro-5-(trifluoromethyl)phenylthanone
7760-76-4 __NOTOC__ Year 776 ( DCCLXXVI) was a leap year starting on Monday (link will display the full calendar) of the Julian calendar. The denomination 776 for this year has been used since the early medieval period, when the Anno Domini calendar era ...
(7). Halogenation with bromine in acetic acid led to 1- -amino-3-chloro-5-(trifluoromethyl)phenyl2-bromoethanone
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(8). Treatment with tert-butylamine 5-64-9yielded 1- -amino-3-chloro-5-(trifluoromethyl)phenyl2-(tert-butylamino)ethenone
CID:13355601
(9). Reduction of the ketone with sodium borohydride completed the synthesis of Mabuterol (10).


See also

*
Clenbuterol Clenbuterol is a sympathomimetic amine used by sufferers of breathing disorders as a decongestant and bronchodilator. People with chronic breathing disorders such as asthma use this as a bronchodilator to make breathing easier. It is most commonl ...
* Cimaterol * Trantinterol (regioisomer)


References

Aromatic amines Chlorobenzenes Phenylethanolamines Tert-butyl compounds Trifluoromethyl compounds {{amine-stub