학술저널
피롤리딘의 개환과 N-프로텍티드 아미노 케톤의 형성; 5-아미노-2-펜타논 유도체의 합성
Ring Opening of Pyrrolidine and Formation of N-Protected Amino Ketones; Synthesis of 5-Amino-2-pentanone Derivatives
- 대한약학회
- 약학회지
- 제40권 제3호 (1996년)
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1996.06300 - 305 (6 pages)
- 2
The base-induced elimination of N-protected 2-(bromomethyl)pyrrolidines 12a-c with KHMDS in THF at -78oC for 1h gave exocyclic enamines 13a-c. The acidic catalyzed protonation on beta-carbon atom of 2-(methylene)pyrrolidines 13a-c. The acidic catalyzed protonation on beta-carbon atom of 2-(methylene)pyrrolidines 13a-c with H3PO4 formed endocyclic N-iminium intermediates 14(or 15). Nucleophilic attack of alpha-carbon atom and hydrolysis of N-iminium ion gave carbocationic adduct (aminoalcohol) 16 from which 5-amino-2-pentanones 17a-c were formed after deprotonation.
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