Synthesis of deuterated clenbuterol

• Published in: Journal of labelled compounds & radiopharmaceuticals Vol. 38; no. 11; pp. 1007 - 1014
• Main Authors: Jørgensen, Ole, Egsgaard, Helge, Larsen, Elfinn
• Format: Journal Article
• Language: English
• Published: Chichester John Wiley & Sons, Ltd 01.11.1996; Wiley
• Subjects: Biochemical Research Methods; Biochemistry & Molecular Biology; Chemistry; Chemistry, Analytical; Chemistry, Medicinal; D3-clenbuterol; D9-clenbuterol; deuterium labelling; Exact sciences and technology; Life Sciences & Biomedicine; mass spectrometry; Noncondensed benzenic compounds; Organic chemistry; Pharmacology & Pharmacy; Physical Sciences; Preparations and properties; Science & Technology; BETA-AGONIST; PLASMA; D-3-clenbuterol; deuterium labelling; LIVER; URINE; D-9-clenbuterol; mass spectrometry; IONIZATION MASS-SPECTROMETRY; RESIDUES; Deuterium; Agonist; Aminoalcohol; Bronchodilator; Benzenic compound; Mass spectrum; Hydrogen Isotopes; Anabolic agent; Chemical synthesis; Labelled compound; Haloamine; β-Adrenergic receptor
• ISSN: 0362-4803; 1099-1344
• DOI: 10.1002/(SICI)1099-1344(199611)38:11<1007::AID-JLCR918>3.0.CO;2-4

The synthesis of D9‐clenbuterol (I) and D3‐clenbuterol (II) is described. D9‐clenbuterol (I) was prepared from 4‐amino‐α‐bromo‐3,5‐dichloroacetophenone by reaction with D9‐tert‐butylamine followed by reduction of the keto group with NaBH4. D3‐clenbuterol (II) was prepared from 4‐amino‐α‐tert‐butylamino‐3,5‐dichloroacetophenone by an exchange reaction of the α‐hydrogens with deuterium followed by reduction of the keto group with NaBD4. The eventual products were characterized by mass spectrometry and NMR.