The synthesis of D-9-clenbuterol (I) and D-3-clenbuterol (II) is descr
ibed. D-9-clenbuterol (I) was prepared from 4-amino-alpha-bromo-3,5-di
chloroacetophenone by reaction with D-9-tert-butylamine followed by re
duction of the keto group with NaBH4. D-3-clenbuterol (II) was prepare
d from ino-alpha-tert-butylamino-3,5-dichloroacetophenone by an exchan
ge reaction of the alpha-hydrogens with deuterium followed by reductio
n of the keto group with NaBD4. The eventual products were characteriz
ed by mass spectrometry and NMR.