Special_Topic_E

Special_Topic_E - P1: PBU/OVY JWDD052-E P2: PBU/OVY QC:...

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P1: PBU/OVY P2: PBU/OVY QC: PBU/OVY T1: PBU Printer: Hamilton JWDD052-E JWDD052-Solomons-v3 April 30, 2007 11:16 E SPECIAL TOPIC Alkaloids SOLUTIONS TO PROBLEMS E.1 (a) The frst step is similar to a crossed Claisen condensation (see Section 19.2A): O EtONa OEt O CH 3 N N O N O CH 3 N + (b) This step involves hydrolysis oF an amide (lactam) and can be carried out with either acid or base. Here we use acid. H HO O heat CH 3 N H 3 O + H 2 O N H CH 3 N N O O (c) This step is the decarboxylation oF a substituted malonic acid; it requires only the application oF heat and takes place during the acid hydrolysis oF step (b). (d) This is the reduction oF a ketone to a secondary alcohol. A variety oF reducing agents can be used, sodium borohydride, For example. OH H CH 3 N NaBH 4 N (e) Here we convert the secondary alcohol to an alkyl bromide with hydrogen bromide; this reagent also gives a hydrobromide salt oF the aliphatic amine. Br - + H CH 3 N H HBr heat N Br 468
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P1: PBU/OVY P2: PBU/OVY QC: PBU/OVY T1: PBU Printer: Hamilton JWDD052-E JWDD052-Solomons-v3
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This note was uploaded on 09/10/2008 for the course CHE 321 taught by Professor Fowler/sampson during the Spring '08 term at SUNY Stony Brook.

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Special_Topic_E - P1: PBU/OVY JWDD052-E P2: PBU/OVY QC:...

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