Solvent-Free Optical Resolution of N-methylamphetamine by Distillation After Partial Diastereoisomeric Salt Formation
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2012-11-20
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Abstract
Solvent-free optical resolution of N-methylamphetamine was developed
by distillation after partial diastereoisomeric salt formation. From the 18 chiral acids
tested by this method, five provide by this method resolution: O,O8-dibenzoyltartaric
acid, O,O8-di-p-toluoyltartaric acid, 6-methoxy-a-methyl-2-naphthaleneacetic acid
(Naproxen), the cis-permetrinic acid, and the 2-phenoxypropionic acid. Among them the
O,O8-dibenzoyltartaric acid in water-free form provided the more effective resolution.
The efficiency of this resolution S = 0.74 is in the range of the industrial-scale resolutions
and not worse than the efficiency achieved by optical resolution via fractional crystallization.
Chirality 13:428–430, 2001. © 2001 Wiley-Liss, Inc
Description
Solvent-free optical resolution of N-methylamphetamine was developed
by distillation after partial diastereoisomeric salt formation. From the 18 chiral acids
tested by this method, five provide by this method resolution: O,O8-dibenzoyltartaric
acid, O,O8-di-p-toluoyltartaric acid, 6-methoxy-a-methyl-2-naphthaleneacetic acid
(Naproxen), the cis-permetrinic acid, and the 2-phenoxypropionic acid. Among them the
O,O8-dibenzoyltartaric acid in water-free form provided the more effective resolution.
The efficiency of this resolution S = 0.74 is in the range of the industrial-scale resolutions
and not worse than the efficiency achieved by optical resolution via fractional crystallization.
Chirality 13:428–430, 2001. © 2001 Wiley-Liss, Inc
Keywords
optical resolution; diastereoisomeric salts; solvent-free process; distillation; O,O8-dibenzoyltartaric acid; O,O8-di-p-toluoyltartaric acid; 6-methoxy- a-methyl-2-naphthaleneacetic acid; cis-permetrinic acid; 2-phenoxypropionic acid