2-(2,3-Dihydro-1H-indol-3-yl)ethanol: synthesis, separation of enantiomers, and assignment of absolute stereochemistry by X-ray structure analysis

Karla Andrea Frydenvang; Michael Bech Sommer; Dieter Heckmann; Ole Nielsen; Benny Bang-Andersen

doi:10.1002/chir.10313

2-(2,3-Dihydro-1H-indol-3-yl)ethanol: synthesis, separation of enantiomers, and assignment of absolute stereochemistry by X-ray structure analysis

Karla Andrea Frydenvang, Michael Bech Sommer, Dieter Heckmann, Ole Nielsen, Benny Bang-Andersen

1 Citation (Scopus)

Abstract

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.

Original language	English
Journal	Chirality
Volume	16
Issue number	2
Pages (from-to)	126-30
Number of pages	5
ISSN	0899-0042
DOIs	https://doi.org/10.1002/chir.10313
Publication status	Published - 2004

Keywords

Chromatography, High Pressure Liquid
Crystallography, X-Ray
Ethanol
Hydrogen
Indoles
Ligands
Models, Molecular
Molecular Conformation
Molecular Structure
Phosphates
Receptors, Dopamine D2
Receptors, Dopamine D4
Stereoisomerism

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10.1002/chir.10313

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title = "2-(2,3-Dihydro-1H-indol-3-yl)ethanol: synthesis, separation of enantiomers, and assignment of absolute stereochemistry by X-ray structure analysis",

abstract = "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.",

keywords = "Chromatography, High Pressure Liquid, Crystallography, X-Ray, Ethanol, Hydrogen, Indoles, Ligands, Models, Molecular, Molecular Conformation, Molecular Structure, Phosphates, Receptors, Dopamine D2, Receptors, Dopamine D4, Stereoisomerism",

author = "Frydenvang, {Karla Andrea} and Sommer, {Michael Bech} and Dieter Heckmann and Ole Nielsen and Benny Bang-Andersen",

year = "2004",

doi = "10.1002/chir.10313",

language = "English",

volume = "16",

pages = "126--30",

journal = "Chirality",

issn = "0899-0042",

publisher = "Wiley",

number = "2",

}

TY - JOUR

T1 - 2-(2,3-Dihydro-1H-indol-3-yl)ethanol

T2 - synthesis, separation of enantiomers, and assignment of absolute stereochemistry by X-ray structure analysis

AU - Frydenvang, Karla Andrea

AU - Sommer, Michael Bech

AU - Heckmann, Dieter

AU - Nielsen, Ole

AU - Bang-Andersen, Benny

PY - 2004

Y1 - 2004

N2 - 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.

AB - 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.

KW - Chromatography, High Pressure Liquid

KW - Crystallography, X-Ray

KW - Ethanol

KW - Hydrogen

KW - Indoles

KW - Ligands

KW - Models, Molecular

KW - Molecular Conformation

KW - Molecular Structure

KW - Phosphates

KW - Receptors, Dopamine D2

KW - Receptors, Dopamine D4

KW - Stereoisomerism

U2 - 10.1002/chir.10313

DO - 10.1002/chir.10313

M3 - Journal article

C2 - 14712476

SN - 0899-0042

VL - 16

SP - 126

EP - 130

JO - Chirality

JF - Chirality

IS - 2

ER -

2-(2,3-Dihydro-1H-indol-3-yl)ethanol: synthesis, separation of enantiomers, and assignment of absolute stereochemistry by X-ray structure analysis

Abstract

Keywords

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