Dolbier HW Solutions 543

Dolbier HW Solutions 543 - nitrogen bond must be formed...

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tution processes. Carbon carbon bond formation with 1-bromo-2,2-dimethylpropane can be achieved more effectively by carboxylation of the corresponding Grignard reagent. The carboxylic acid can then be converted to the desired amine by reduction of the derived amide. The yields listed in parentheses are those reported in the chemical literature for this synthesis. ( b ) Consider the starting materials in relation to the desired product. The synthetic tasks are to form the necessary carbon nitrogen bond and to reduce the carbonyl group to a methylene group. This has been accomplished by way of the amide as a key inter- mediate. A second approach utilizes reductive amination following conversion of the starting car- boxylic acid to an aldehyde. The reducing agent in the reductive amination process cannot be hydrogen, because that would result in hydrogenation of the double bond. Sodium cyanoborohydride is required. ( c ) It is stereochemistry that determines the choice of which synthetic method to employ in in- troducing the amine group. The carbon
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Unformatted text preview: nitrogen bond must be formed with inversion of 10-Undecenal H 2 C CH(CH 2 ) 8 CH O NaBH 3 CN 1 Pyrrolidine N-(10-Undecenyl)pyrrolidine H 2 C CH(CH 2 ) 8 CH 2 N N H 10-Undecenoic acid H 2 C CH(CH 2 ) 8 COH O 10-Undecenal H 2 C CH(CH 2 ) 8 CH O 10-Undecen-1-ol H 2 C CH(CH 2 ) 8 CH 2 OH PCC or PDC CH 2 Cl 2 1. LiAlH 4 2. H 2 O 10-Undecenoic acid H 2 C CH(CH 2 ) 8 COH O N-(10-Undecenoyl)pyrrolidine (75%) O H 2 C CH(CH 2 ) 8 C N N-(10-Undecenyl)pyrrolidine (66%) H 2 C CH(CH 2 ) 8 CH 2 N 1. SOCl 2 2. pyrrolidine 1. LiAlH 4 2. H 2 O 1 Pyrrolidine N H 10-Undecenoic acid H 2 C CH(CH 2 ) 8 COH O N-(10-Undecenyl)pyrrolidine H 2 C CH(CH 2 ) 8 CH 2 N 3,3-Dimethylbutanoic acid (CH 3 ) 3 CCH 2 CO 2 H 3,3-Dimethyl-1-butanamine (57%) (CH 3 ) 3 CCH 2 CH 2 NH 2 1. SOCl 2 2. NH 3 1. LiAlH 4 2. H 2 O 3,3-Dimethylbutanamide (51%) (CH 3 ) 3 CCH 2 CNH 2 O 1-Bromo-2,2-dimethylpropane (CH 3 ) 3 CCH 2 Br 3,3-Dimethylbutanoic acid (63%) (CH 3 ) 3 CCH 2 CO 2 H 1. Mg 2. CO 2 3. H 3 O 1 AMINES 637...
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