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KMID : 0370219960400030300
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Yakhak Hoeji
1996 Volume.40 No. 3 p.300 ~ p.305
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Ring Opening of Pyrrolidine and Formation of N-Protected Amino Ketones; Synthesis of 5-Amino-2-pentanone Derivatives
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박명숙/Park MS
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Abstract
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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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KEYWORD
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