Chemistry:Bornaprolol

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Bornaprolol is a beta-adrenergic antagonist.[1]

Synthesis

ChemDrug Synthesis:[2][3] Patent:[4]

The reaction between 2-(Bicyclo[2.2.1]hept-2-yl)phenol [17152-43-1] (1) and epichlorohydrin [106-89-8] (2) in the presence of sodium metal gives (3). Opening of the oxirane by treatment with isopropylamine [75-31-0] (4) completed the synthesis of Bornaprolol (5).

References

  1. ↑ Cheymol, G; Jaillon, P; Lecoq, B; Lecoq, V; Cheymol, A; Krumenacker, M (1987). "Cardiovascular beta-adrenergic blocking effects of bornaprolol in humans: Relation to dose and plasma concentration". Journal of Cardiovascular Pharmacology 9 (6): 694–8. doi:10.1097/00005344-198706000-00009. PMID 2442536. 
  2. ↑ Michaud, R.; Bornaprolol hydrochloride. Drugs Fut 1982, 7, 2, 91.
  3. ↑ Hardy, J.C. et al, Bull. Soc. Chim. Fr., Part 2, 1982, 304.
  4. ↑ DE2735570 idem Jean Mardiguian, U.S. Patent 4,157,400 (1985 to Marpha Societe D'etudes Et D'exploitation De Marques S.A., Paris, Fr).