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  • High-performance liquid chromatographic resolution of enantiomers of 1-phenyl-2-aminopropanes (amphetamines) with four chiral reagents.

High-performance liquid chromatographic resolution of enantiomers of 1-phenyl-2-aminopropanes (amphetamines) with four chiral reagents.

Journal of chromatography (1984-05-11)
K J Miller, J Gal, M M Ames
ABSTRACT

High-performance liquid chromatography (HPLC) was employed for resolution of enantiomers of chiral ring-substituted 1-phenyl-2- aminopropanes (amphetamines) and 1-phenylethylamine following derivatization with four chiral reagents: (R)-(+)-1-phenylethyl isocyanate ( PEIC ), (-)-alpha-methoxy-alpha-(trifluoromethyl)phenylacetyl chloride ( MTPA X Cl), 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl isothiocyanate ( GITC ), and 2,3,4-tri-O-acetyl-alpha-D- arabinopyranosyl isothiocyanate ( AITC ). Reactions were accomplished under mild conditions (25-70 degrees C) and were complete for all substrates within 60 min. Derivatization with the sugar isothiocyanates ( GITC and AITC ) and the acyl chloride ( MTPA . Cl) was carried out in methylene chloride or acetonitrile in the presence of a base catalyst while derivatization with the isocyanate ( PEIC ) was performed in methylene chloride. The diastereomeric derivatives were separated by reversed-phase HPLC (C18) with a methanol-water mobile phase. In general, HPLC resolution of the diastereomeric reaction products of GITC or AITC , and MTPA .Cl with the amine substrates was more complete (usually greater than 98% baseline separation) than HPLC resolution of the diastereomeric reaction products of PEIC .

MATERIALS
Product Number
Brand
Product Description

Supelco
(S)-(+)-α-Methoxy-α-(trifluoromethyl)phenylacetyl chloride, for chiral derivatization, LiChropur, ≥99.0%
Sigma-Aldrich
(S)-(+)-α-Methoxy-α-(trifluoromethyl)phenylacetyl chloride, 99%
Sigma-Aldrich
Phenethyl isocyanate, 98%
Supelco
2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl isothiocyanate, for chiral derivatization, LiChropur, ≥98.0% (HPLC)
Supelco
(R)-(−)-α-Methoxy-α-(trifluoromethyl)phenylacetyl chloride, for chiral derivatization, LiChropur, ≥99.0%