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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?

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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

Devise a synthesis of each compound from benzene, any organic alcohols having four carbons or fewer, and any required reagents.

a

b

c

Draw the products formed when each amine is treated with [1] CH3I(excess); [2] Ag2O; [3] 鈭�. Indicate the major product when a mixture results.

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Question: Name each amine.

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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.

Draw the product of each reductive amination reaction.

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