Английская Википедия:2-Carbomethoxytropinone

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2-Carbomethoxytropinone (2-CMT) is a commonly used organic intermediate in the synthesis of cocaine and its analogues.[1] As of at least 1999 no reaction pathway has been discovered that synthesizes cocaine-like compounds without utilizing the reduction of 2-CMT.[2] The structure of cocaine was discovered by Richard Willstätter in 1898 after he synthesized it from 2-carbomethoxytropinone.[3][4] Although it was originally believed that 2-CMT in nature was ultimately derived from ornithine and acetic acid,[5] subsequent research has indicated other pathways exist for the biosynthesis of 2-CMT.[6][7] A β-keto ester, 2-CMT exists in equilibrium with its keto–enol tautomer.

Synthesis

2-CMT (3) can be synthesized from 1,3-acetonedicarboxylate anhydride (1) by methanolysis followed by reaction with methylamine and succinaldehyde.[8]

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Synthesis of 2-CMT
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See also

References

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