Preparation of trimethylsilyl ethers of 3??azetidinols. Scope and Limitations

RH Higgins, MR Watson, WJ Faircloth…

Index: Higgins, Robert H.; Watson, Monique R.; Faircloth, William J.; Eaton, Quentin L.; Jenkins, Harvey Journal of Heterocyclic Chemistry, 1988 , vol. 25, p. 383 - 387

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Citation Number: 15

Abstract

Abstract Preparation of the trimethylsilyl ethers of 1-alkyl-3-azetidinols from non-hindered primary amines and epichlorohydrin by conversion of the intermediate 1-(alkylamino)-3- chloro-2-propanols to their trimethylsilyl ethers by either N-(trimethylsilyl) acetamide or by 1- (trimethylsilyl) imidazole followed by ring closure in acetonitrile is described. This sequence of reactions fails for aromatic amines, but appears to be general for all primary aliphatic ...