Interpretation: The given compound of amine is to be prepared via reductive amination and preparation of the starting material via retrosynthetic analysis of the final product.
Concept Introduction: Sodium cyanoborohydride is a strong reducing agent than sodium borohydride. It reduces the carbonyl group into amine group in a rapid way. So, it is called as reductive amination reactions.
Aldehyde or ketone group is reacted with primary amine in the presence of sodium cyanoborohydride as a reducing agent and a proton source in the reaction medium to produce secondary amines.
Aldehyde or ketone group is reacted with secondary amine in the presence of sodium cyanoborohydride as a reducing agent and a proton source in the reaction medium to produce tertiary amines.
There are two ways to get the starting compounds in either left or right side cleavage of all C−N bonds. After the cleavage, retrosynthetic analysis of the starting materials is done. If both aldehyde/ketone and amine starting materials are decided, reductive amination is followed in both the ways by placing the suitable reagents.
The starting materials for reductive amination are carbonyl compound and alkyl amine. The carbonyl compound can be prepared in a number of ways such as radical bromination of
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Chapter 22 Solutions
Organic Chemistry
- 16. The proton NMR spectral information shown in this problem is for a compound with formula CioH,N. Expansions are shown for the region from 8.7 to 7.0 ppm. The normal carbon-13 spec- tral results, including DEPT-135 and DEPT-90 results, are tabulated: 7 J Normal Carbon DEPT-135 DEPT-90 19 ppm Positive No peak 122 Positive Positive cus и 124 Positive Positive 126 Positive Positive 128 No peak No peak 4° 129 Positive Positive 130 Positive Positive (144 No peak No peak 148 No peak No peak 150 Positive Positive してしarrow_forward3. Propose a synthesis for the following transformation. Do not draw an arrow-pushing mechanism below, but make sure to draw the product of each proposed step (3 points). + En CN CNarrow_forwardShow work..don't give Ai generated solution...arrow_forward
- Label the spectrum with spectroscopyarrow_forwardQ1: Draw the most stable and the least stable Newman projections about the C2-C3 bond for each of the following isomers (A-C). Are the barriers to rotation identical for enantiomers A and B? How about the diastereomers (A versus C or B versus C)? enantiomers H Br H Br (S) CH3 H3C (S) (R) CH3 H3C H Br A Br H C H Br H3C (R) B (R)CH3 H Br H Br H3C (R) (S) CH3 Br H D identicalarrow_forwardLabel the spectrumarrow_forward
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