Process for Producing Aziridine Compounds

Ishii etaU US Patent 6,323,346 (November 27, 2001) Assignee Daicel Chemical Industries, Ltd. 

Utility Amino Acid and j8-Lactam Antibiotic Intermediates 

A mixture of N-butylidenebutylimine (0.5 mol), ethyl diazoacetate (0.5), di-/x-chloro-tetrakis(cyclooctene)diirridium(I) (0.015 mol), and 0.5 ml THE were stirred at ambient temperature three hours and the product isolated in 29% yield. 

The author also performed this catalytic reaction using insitu generated imines. Thus when n-butylamine was reacted with butyraldehyde at —5°C in THE containing ethyl diazoacetate, l,3-di-n-dutyl-3-ethoxycarbonylaziridine was isolated in 74% yield. 

In earlier investigations, the author developed catalytic methods for preparing ketones and poly ketones using acetylacetonato-vanadium(III) (1). Oxidative process for ethers using acetylacetonatocobalt(II) are also described by the author (2). 

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