Smooth Azalea – Rhododendron arborescens

by | Dec 19, 2023 | Azalea

How Can We Help?
You are here:
< Back

Bopindolol (INN) is a beta blocker. It is an ester which acts as a prodrug for its active metabolite 4-(3-t-butylamino-2-hydroxypropoxy)-2-methylindole.[1]

Synthesis

Thieme Patent:[2] Starting amnine:[3]

The reaction of 4-Hydroxy-2-methylindole [35320-67-3] (1) with epichlorohydrin in the presence of lye led to 2-methyl-4-(oxiran-2-ylmethoxy)-1H-indole [62119-47-5] (2). Addition of tert-butylamine led to 4-(2-Hydroxy-3-tert-butylaminopropoxy)-2-methylindole [23869-98-9] (3). Ester formation with benzoic anhydride [93-97-0] (4) in the presence of hexamethylphosphoric acid triamide [680-31-9] completed the synthesis of Bopindolol (5).

See also

References

  1. ^ Nagatomo T, Hosohata Y, Ohnuki T, Nakamura T, Hattori K, Suzuki J, Ishiguro M (Spring 2001). "Bopindolol: pharmacological basis and clinical implications". Cardiovascular Drug Reviews. 19 (1): 9–24. doi:10.1111/j.1527-3466.2001.tb00180.x. PMID 11314603.
  2. ^ DE2635209 idem Franz Troxler, Fritz Seemann, U.S. patent 4,434,176 (1984 to Sandoz Ltd.).
  3. ^ Franz Dr Troxler & Albert Dr Hofmann, CH453363 (1968 to Sandoz AG).
Categories
Table of Contents