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 alcohol4. 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.
↑DE 2728641,Philion, Richard Everett,"4-Hydroxyphenylalkanolaminderivate und Verfahren zu deren Herstellung [4-Hydroxyphenylalkanolamine derivatives and processes preparation thereof]",published 1978-01-05, assigned to Sterling Drug Inc.
↑R. E. Philion, (1978 to Sterling), C.A. 90, 137468 (1979)
