2-Carbomethoxytropinone (2-CMT) is a commonly used

organic Organic may refer to: * Organic, of or relating to an organism, a living entity * Organic, of or relating to an anatomical organ Chemistry * Organic matter, matter that has come from a once-living organism, is capable of decay or is the product ...

intermediate in the

synthesis Synthesis or synthesize may refer to: Science Chemistry and biochemistry *Chemical synthesis, the execution of chemical reactions to form a more complex molecule from chemical precursors **Organic synthesis, the chemical synthesis of organi ...

cocaine Cocaine is a tropane alkaloid and central nervous system stimulant, derived primarily from the leaves of two South American coca plants, ''Erythroxylum coca'' and ''Erythroxylum novogranatense, E. novogranatense'', which are cultivated a ...

and its analogues. As of at least 1999 no reaction pathway has been discovered that synthesizes cocaine-like compounds without utilizing the reduction of 2-CMT. The structure of cocaine was discovered by

Richard Willstätter Richard Martin Willstätter FRS(For) HFRSE (, 13 August 1872 – 3 August 1942) was a German organic chemist whose study of the structure of plant pigments, chlorophyll included, won him the 1915 Nobel Prize for Chemistry. Life Willstätter wa ...

in 1898 after he synthesized it from 2-carbomethoxytropinone. Although it was originally believed that 2-CMT in nature was ultimately derived from

ornithine Ornithine is a non-proteinogenic α-amino acid that plays a role in the urea cycle. It is not incorporated into proteins during translation. Ornithine is abnormally accumulated in the body in ornithine transcarbamylase deficiency, a disorder of th ...

and

acetic acid Acetic acid , systematically named ethanoic acid , is an acidic, colourless liquid and organic compound with the chemical formula (also written as , , or ). Vinegar is at least 4% acetic acid by volume, making acetic acid the main compone ...

, subsequent research has indicated other pathways exist for the biosynthesis of 2-CMT. A β-keto ester, 2-CMT exists in equilibrium with its keto–enol

tautomer In chemistry, tautomers () are structural isomers (constitutional isomers) of chemical compounds that readily interconvert. The chemical reaction interconverting the two is called tautomerization. This conversion commonly results from the reloca ...

Synthesis

2-CMT (3) can be synthesized from 1,3-acetonedicarboxylate anhydride (1) by

methanolysis Transesterification is the process of exchanging the organic functional group R″ of an ester with the organic group R' of an alcohol. These reactions are often catalyzed by the addition of an acid or base catalyst. Strong acids catalyze the r ...

followed by reaction with

methylamine Methylamine, also known as methanamine, is an organic compound with a formula of . This colorless gas is a derivative of ammonia, but with one hydrogen atom being replaced by a methyl group. It is the simplest primary amine. Methylamine is sold ...

and

succinaldehyde Succinaldehyde or Butanedial is an organic compound with the formula . It is a colorless viscous liquid. Typical of some other saturated dialdehydes, succinaldehyde is handled as the hydrates or methanol-derived acetal. It is a precursor to tropi ...

.Proc F. according to Findlay : 2-Carbomethoxytropinone_synthesis

References

{{DEFAULTSORT:Carbomethoxytropinone, 2- Tropanes Ketones Methyl esters

Synthesis

See also

References