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By Bancroft W.D., Barnett C.E.

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Catalytic reduction leads to medroxaiol (32) , The methyl group on a sulfoxide interestingly proves sufficiently acidic to substitute for phenolic hydroxyl. The preparation of this combined a- and 3-blocker, suifinalol6, begins by protection of the phenolic hydroxyl as its benzoate ester (34). Bromination (35) followed by 26 PHENETHYL AND PHENOXYPROPANOLAMINES condensation with amine j36^ gives the aminoketone (37). Successive catalytic reduction and saponification affords the aminoalcohol (j$8h Oxidation of the sulfide to he sulfoxide with a reagent such as metaperiodate gives suifinaioi (39).

L. S. Patent 3,929,897 (1975); Chem. , 85, 32426q (1976). 2 Phenethyl and Phenoxypropanolamines The phenylethanolamine derivatives epinephrine (1) and norepinephrine (2) are intimately associated with the sympathetic nervous system. These two neurotransmitter hor- (1) R = CH 3 (2) R = H (3) R = (4) mones control many of the responses of this branch of the involuntary, autonomic nervous system. Many of the familiar responses of the "fight or flight" syndrome such as vasoconstriction, increase in heart rate, and the like are mediated by these molecules.

24 PHENETHYL AND PHENOXYPROPANOLAMINES (19) )-V^ yui y-ClL CIU Clt N IC CH^ CH-Y y-(X:GI_3 NUJC 2cn 2cn \ / Z 2 i CI O iH\^~"^ / r> (22) (20) (21) *- IK)-V ^ yy-O[ i 2CcI-V ^ V y-C 2 ao(3l 2,aiNH GL, \ / L IQ\ * ZO•il \ / Drugs that block the action of a-adrenergic activation effectively lower blood pressure by opposing the vasoconstricting effects of norepinephrine. Drawbacks of these agents, which include acceleration of heart rate, orthostatic hypotension and fluid retention, were at one time considered to be due to the extension of the pharmacology of a-blockers.

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Pentavalent nitrogen in organic compounds by Bancroft W.D., Barnett C.E.


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