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Chapter 25: PROBLEM 25.14 (page 1012)

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

Short Answer

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Answer

Step by step solution

01

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.

02

Reduction of imine to amine

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

03

Explanation

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

Formation of the product enalapril by the reduction of ketone

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Most popular questions from this chapter

Why is pyrrole more acidic than pyrrolidine?

Question: Safrole, which is isolated from sassafras (Problem 21.33), can be converted to the illegal stimulant MDMA (3,4-methylenedioxymethamphetamine, 鈥淓cstasy鈥�) 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.

Question: Arrange the compounds in order of increasing boiling point.

Question: Draw the products formed when each carbonyl compound reacts with the following amines:

1. CH3CH2CH2NH2

2.(CH3CH2)2NH

a.

b.

c.

Question: Draw the major product formed in each reaction.

a.

b.

c.

d.
See all solutions

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