Method for synthesizing 2-carbomethoxytropinone

Details Method for synthesizing 2-carbomethoxytropinone Method for synthesizing 2-carbomethoxytropinone

2005-12-16

2010-12-21

Seaman, D. Margaret (Department: 1625)

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C546S132000

Reexamination Certificate

active

07855296

ABSTRACT:
Disclosed is a method of making (−)-cocaine efficient for use on a large scale. The cocaine is created by reacting an aqueous solution of (+)-2-carbomethoxytropinone (2-CMT) bitartrate, sodium amalgam and an acid that forms a highly soluble sodium salt to form (−)-methylecgonine. (−)-Methylecgonine is converted into (−)-cocaine. Sodium amalgam is continuously supplied from an electrolyzing unit to a reactor containing the aqueous solution of (+)-2-carbomethoxytropinone bitartrate and spent amalgam is continuously removed and regenerated. The aqueous solution is prepared by adding (rac)-2-CMT in chloroform to a solution of (+)-tartaric acid in water to create an aqueous phase having diastereomeric salts of 2-CMT with (+)-tartaric acid. An organic solvent is added to the aqueous phase and the crystals obtained from the combined aqueous phase and organic solvent are dried to obtain substantially pure crystalline (+)-2-carbomethoxytropinone bitartrate. The (rac)-2-CMT in chloroform is prepared by extracting 2-CMT from a citric acid solution.

REFERENCES:
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Findlay S.P.Concerning 2-Carbomethoxytropinone. 2-Carbomethoxytropinone, Nov. 1957, 1385-1394.
Lin R. et al.Enantiospecific Synthesis of Natural (−)-Cocaine and Unnatural (+)-Cocaine from D- and L-Glutamic Acid. J. Org. Chem 1998, 63, 4069-4078.
Mans D.M. et al.Total Synthesis of (+)-Cocaine via Desymmetrization of a meso-Dialdehyde. Organic Letters, vol. 6, No. 19, 2004, 3305-3308.

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