PROBLEM 25.68 - Organic Chemistry

Question

Question: Safrole, which is isolated from sassafras (Problem 21.33), can be converted to the illegal stimulant MDMA (3,4-methylenedioxymethamphetamine, “Ecstasy”) by a variety of methods. (a) Devise a synthesis that begins with safrole and uses a nucleophilic substitution reaction to introduce the amine. (b) Devise a synthesis that begins with safrole and uses reductive amination to introduce the amine.

Step-by-Step Solution

Answer

Answer

a.

Nucleophilic substitution method

b.

Nucleophilic substitution reaction

The double bond on the acyclic carbon chain is reduced, and a hydroxide OH^- group is introduced with a reducing agent in the presence of a base. 

The amine group is then introduced by substituting the hydroxide group with suitable more nucleophilic groups. 

Reductive amination

The conversion of the carbonyl group into an imine group followed by the conversion into an amine group is known as the reductive amination reaction.

Products of the given reaction

a.The product formed by the nucleophilic substitution method is shown hereunder

Nucleophilic substitution method

b. The product formed by the reductive amination method is shown hereunder.