1830-39-3Relevant academic research and scientific papers
The Resolution and Absolute Configuration by X-Ray Crystallography of the Isomeric Octopamines and Synephrines
Midgley, John M.,Thonoor, Mohan C.,Drake, Alex F.,Williams, Clyde M.,Koziol, Anna E.,Palenik, Gus J.
, p. 963 - 970 (2007/10/02)
Racemates of the naturally occuring biogenic amines, o-, m-, and p-octopamine and p-synephrine, have been resolved by the preparation of suitable diastereomeric salts with antipodes of appropriate organic acids.The circular dichroism (c.d.) curves of (-)-m-octopamine hydrochloride and (-)-m-synephrine hydrochloride were superimposable and of opposite sign to those of the corresponding (-)-p-derivatives.X-ray crystallography of the (-)-3-bromocamphor-8-sulphonate salt of (-)-p-synephrine confirmed (for the first time by direct means in this series of compounds) that the absolute configuration of (-)-p-synephrine is R.It is concluded from the c.d. data that the absolute configuration of (-)-p-octopamine is also R.
