5R-Methyl-1-chloromethyl-2-pyrrolidinone: Determining Enantiomeric Excess in Chiral Nonracemic Amines¹

Ping Chen Room 151, 215 Glenbrook Rd., Department of Chemistry, University of Connecticut, Storrs, Connecticut, 06269-4060 E-mail: [email protected]

Sheiwei Tao Room 151, 215 Glenbrook Rd., Department of Chemistry, University of Connecticut, Storrs, Connecticut, 06269-4060 E-mail: [email protected]

Michael B. Smith Room 151, 215 Glenbrook Rd., Department of Chemistry, University of Connecticut, Storrs, Connecticut, 06269-4060 E-mail: [email protected]

Abstract

5R-Methyl-1-chloromethyl-2-pyrrolidinone reacts with chiral, racemic amines to form a diastereomeric adduct. Analysis of the N-CH₂-O signals in the proton NMR spectra allows determination of the enantiomeric excess of the original amine.

Notes

Presented in part at the 207th National Meeting of the American Chemical Society, ORGN 30, San Diego, CA. and at the 209th National Meeting of the American Chemical Society, ORGN 287, Anaheim, CA.

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5R-Methyl-1-chloromethyl-2-pyrrolidinone: Determining Enantiomeric Excess in Chiral Nonracemic Amines¹

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5R-Methyl-1-chloromethyl-2-pyrrolidinone: Determining Enantiomeric Excess in Chiral Nonracemic Amines1

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5R-Methyl-1-chloromethyl-2-pyrrolidinone: Determining Enantiomeric Excess in Chiral Nonracemic Amines¹