Question

Question: Cinnamoylcocaine, a natural product that occurs in coca leaves, can be converted tococaine by the following reaction sequence. Identify the structure of cinnamoylcocaine, aswell as intermediates X and Y.

Short answer

Answer

Step-by-step solution

Step-by-Step SolutionStep 1: Cinnamoylcocaine

Cinnamoylcocaine is a common name for the compound methylecgoninecinnamate. This compound is regarded to be pharmacologically inactive

Cocaine

Cocaine belongs to the category of alkaloids. It is employed as a recreational drug as well as euphoriant.

Structure of cinnamoylcocaine and the intermediates X and Y

In the presence of ${\mathrm{NaOCH}}_3\mathrm{and}{\mathrm{CH}}_3\mathrm{I}$alkylation happens at the secondary amine. This denotes that compound Y comprises a secondary amine group that gets subjected to alkylation leading to the formation of cocaine. The possible structure of Y and the chemical reaction can be given as:

Possible structure of Y

The PhCOOCOPh acquires acidic proton from the alcoholic group leading to the formation of benzoic anhydride. Hence, compound X contains an alcoholic group. The structure of X and the chemical reaction can be given as:

Structure of X

The reaction for the formation of cinnamoylcocaine can be given as:

Reaction for the formation of cinnamoylcocaine