피롤리딘의 개환과 N-프로텍티드 아미노 케톤의 형성; 5-아미노-2-펜타논 유도체의 합성

• 영문명: Ring Opening of Pyrrolidine and Formation of N-Protected Amino Ketones; Synthesis of 5-Amino-2-pentanone Derivatives
• 발행기관: 대한약학회
• 저자명: 박명숙(Myung Sook Park)
• 간행물 정보: 『약학회지』제40권 제3호 (1996년), 300~305쪽, 전체 6쪽
• 주제분류: 의약학 > 기타의약학
• 파일형태: PDF
• 발행일자: 1996.06.30

영문 초록

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.

키워드

Base-induced elimination of alkyl halides Formation of enamines Hydrolysis of N-iminium intermediates Synthesis of amino ketones (5-amino-2-pentanones).