Synthesis of (-)-.beta.-methoxysynephrine

Cactaceae Alkaloids XVIII: Two New Alkaloids from Coryphantha Calipensis H. Bravo

“…The sympathomimetic drug (-)-synephrine (III), closely related to norepinephrine, has been isolated from citrus leaves (18) and various COOphantha species (9,15,19). Similar in structure to the now isolated methyl ethers of macromerine and normacromerine is (-)$-0-methylsynephrine (IV), found in tangerine leaves by Stewart and Wheaton (14). These researchers suggested that this compound could be an artifact from their extraction process.…”

“…Comparison with VIII showed the two compounds to be identical in all respects [NMR, IR (chloroform), mass spectroscopy, TLC, GLC, melting point, and mixed melting point]. (*)-N.N-Dimethyl-3,4-dimethoxy-P-methoxyphenethylamine was also prepared from (*)macromerine (11) by refluxing a solution of the latter compound in 2 N HCI in methanol (14). The product, isolated by preparative TLC, was identical with VIII and the N-methyl derivative of VII [TLC, GLC, NMR, IR (chloroform), and mass spectroscopy].…”

Cactus Alkaloids XII: β-Phenethylamine Alkaloids of the Genus Coryphantha

“…181.1 103) and a base peak at /ri/c. 137 (34); after recrystalli7ation, it melted a t 180-182' and gave N M R spectra identical to that of P. These authors suggest that this product was an artifact of their isolation procedure and synthesized ~-O-mctliylsyneplirine by eluting synephrine from an acidic Dowcx column with 2 N N a O H in methanol (34). I n this laboratory, the hasic Amhcrlite column used in the isolation procedure did not convert reference syncphrine to the ~-O -m e t h y l dcrivative, a s evidenced by TLC.…”

Some potentially physiologically active β, β-diphenylethylamines derived from adrenaline

“…The formation of different types of products including P-phenylnaphthalene derivatives (6,7) and phenylacetaldehyde and phenylacetone derivatives (8)(9)(10) by the action of strong mineral acids on P-phenylethanolamines in general has also been reported. Furthermore it is well known that in the presence of acids, aliphatic alcohols form ethers with the secondary alcohol function of some P-phenylethanolamines (3,4,(11)(12)(13)(14).…”