PRODUCTION OF OPTICALLY ACTIVE 2-PYRROLIDINONE

摘要

PURPOSE: To efficiently obtain the subject compound having optical activity and useful as an intermediate of antimicrobial agents for medicines by carrying out cyclization reaction of a specific compound in the presence of a base. CONSTITUTION: A compound of formula I (X is an eliminable group; R<1> is H or a protecting group of OH group; R<2> is H, a lower alkyl or a protecting group of an amino group) having S coordination or R coordination is subjected to cyclization reaction (e.g. in an organic solvent at -78 deg.C to ambient temperature for 30min to 5hr) in the presence of a base (e.g. sodium hydroxide in an amount of 1-3 times by mol based on the compound of formula I) to provide the objective compound of formula II having S coordination or R coordination [e.g. (S)-1-benzyl-4-tert.-butyldimethylsilyloxy-2-pyrrolidinone]. Furthermore, deprotecting is preferably carried out after the cyclization reaction.