Oxidation of 3-hydroxypiperidines with iodosylbenzene in water: Tandem oxidative grob fragmentation-cyclization reaction

Chemical and Pharmaceutical Bulletin

Volumn 52, Issue 9, 2004, Pages 1143-1144

  Tada, Norihiro ^a   Miyamoto, Kazunori ^a   Ochiai, Masahito ^a  

^a UNIVERSITY OF TOKUSHIMA   (Japan)

Author keywords

3 hydroxypiperidine; Amino alcohol; Grob fragmentation; Iodane; Iodosylbenzene; Water

Indexed keywords

2 PYRROLIDINONE; 3 PIPERIDINOL; ALDEHYDE; AMINOALCOHOL; IODOSOBENZENE; PIPERIDINE DERIVATIVE; UNCLASSIFIED DRUG; WATER; IODOBENZENE;

ARTICLE; CHEMICAL MODIFICATION; CYCLIZATION; FRAGMENTATION REACTION; HYDROLYSIS; OXIDATION; CHEMICAL STRUCTURE; CHEMISTRY; OXIDATION REDUCTION REACTION;

CYCLIZATION; IODOBENZENES; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PIPERIDINES; WATER;

EID: 16644400310     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.52.1143     Document Type: Article

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16. A referee pointed out the possible formation of 2-pyrrolidinone (2) and the cyclic aminal 10 by the decomposition of N-hyroxymethyl-2-pyrrolidinone (4) and the diol 11 under these conditions, respectively. The fact that exposure of 4 to water for 24 h under ambient conditions afforded 2-pyrrolidinone (2) in only 4% yield and that 86% of 4 was recovered unchanged may suggest the involvement of the decomposition pathways of 4 and 11, but the contribution of the process is not important in our reactions.