PROBLEM 25.14 - Organic Chemistry

Question

Question: Enalapril, a drug used to treat hypertension, is prepared from compounds D and E by reductive amination. What is the structure of enalapril?

Step-by-Step Solution

Answer

Answer

Reduction of aldehyde to amine

The carbonyl carbon of the aldehyde or ketone is reduced by the attack of an amine group.  

The electron pair donated by the amine group is accepted by the electron-deficient C=O. 

Reduction of imine to amine

Reducing agents such as sodium cyanoborohydride are used to reduce imine to primary, secondary, or tertiary amine.

Explanation

The given ketone compound is reduced to amine, as shown below.

Formation of the product enalapril by the reduction of ketone