2-(2,3-Dihydro-1H-indol-3-yl)ethanol: synthesis, separation of enantiomers, and assignment of absolute stereochemistry by X-ray structure analysis.
The first direct resolution of racemic 2-(2,3-dihydro-lH-indol-3-yl)ethanol-prepared by catalytic hydrogenation of 2-(lH-indol-3-yl)ethanol-has been accomplished by chiral simulated moving bed (SMB) chromatography. The single enantiomers were isolated as their dihydrogen phosphate salts. Single-crystal X-ray analyses were successful, revealing that the (+)-enantiomer of 2-(2,3-dihydro-lH-indol-3-yl)ethanol has the (S) configuration. Chirality 16:126-130, 2004.
Frydenvang
Karla
K
Department of Medicinal Chemistry, The Danish University of Pharmaceutical Sciences, Copenhagen, Denmark. kf@dfuni.dk
Sommer
Michael Bech
MB
Heckmann
Dieter
D
Nielsen
Ole
O
Bang-Andersen
Benny
B
D002851:Chromatography, High Pressure Liquid; D018360:Crystallography, X-Ray; D000431:Ethanol / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry*; D006859:Hydrogen / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry*; D008024:Ligands; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D010710:Phosphates / Q000737:chemistry; D017448:Receptors, Dopamine D2 / Q000819:agonists; D050638:Receptors, Dopamine D4; D013237:Stereoisomerism
C488843:2-(2,3-dihydro-1H-indol-3-yl)ethanol; D007211:Indoles; D008024:Ligands; D010710:Phosphates; D017448:Receptors, Dopamine D2; D050638:Receptors, Dopamine D4; D000431:Ethanol; D006859:Hydrogen