Chemistry:Sulfinalol
From HandWiki
Sulfinalol is a beta adrenergic receptor antagonist.[1]
Synthesis
The preparation of sulfinalol begins by protection of the phenolic hydroxyl as its benzoate ester. Bromination followed by condensation with 4-(4-methoxyphenyl)butan-2-amine gives the amino ketone 3. Successive catalytic reduction and saponification affords amino alcohol 4. Oxidation of the sulfide to the sulfoxide with a reagent such as metaperiodate gives sulfinalol (5).
The methyl group on a sulfoxide is sufficiently acidic to substitute for phenolic hydroxyl.
References
- ↑ Sybertz, E. J.; Baum, T.; Pula, K. K.; Nelson, S.; Eynon, E.; Sabin, C. (1982). "Studies on the mechanism of the acute antihypertensive and vasodilator actions of several beta-adrenoceptor antagonists". J. Cardiovasc. Pharmacol. 4 (5): 749–58. doi:10.1097/00005344-198209000-00009. PMID 6182405.
- ↑ Philion, Richard Everett, "4-Hydroxyphenylalkanolaminderivate und Verfahren zu deren Herstellung [4-Hydroxyphenylalkanolamine derivatives and processes preparation thereof]", DE patent 2728641, published 1978-01-05
- ↑ R. E. Philion, (1978 to Sterling), C.A. 90, 137468 (1979)
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