A convenient and inexpensive conversion of an aziridine to an oxazolidinone

Tetrahedron Letters

Volumn 44, Issue 29, 2003, Pages 5457-5460

  Hancock, Matthew T ^a   Pinhas, Allan R ^a  

^a UNIVERSITY OF CINCINNATI   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AZIRIDINE; CARBON DIOXIDE; HEMPA; IODIDE; LITHIUM DERIVATIVE; OXAZOLIDINONE DERIVATIVE;

ARTICLE; CATALYSIS; DRUG COST; DRUG SYNTHESIS; STEREOCHEMISTRY;

EID: 0037863152     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01325-X     Document Type: Article

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25. 1H NMR spectrum for each compound. It has been shown in the literature (Wohl, R. A. J. Org. Chem. 1973, 38, 3858) that for similar oxazolidinones, the methyl groups at C-4 and C-5 are at higher field in the cis isomer than in the trans isomer, and the methine protons at C-4 and C-5 are at lower field in the cis isomer than in the trans isomer.
26. 3, and evaporated to dryness yielding the oxazolidinone. Method B for the conversion of an aziridine to an oxazolidinone with or without added HMPA. A mixture of 0.4 mmol aziridine, 0.1 or 0.4 mmol lithium iodide, and 0.4 mmol HMPA (when needed) in 15 mL of THF was added to a 25 mL heavy walled round bottom flask that contained a threaded Teflon plug. This reaction mixture was then cooled to -78°C, and 8.0 g (180 mmol) of powdered dry ice (carbon dioxide) was added in two portions. The round bottom flask was then capped with the threaded Teflon plug and allowed to warm to room temperature. The reaction mixture was stirred overnight at room temperature. After that, the mixture was again cooled to -78°C and the pressure was released very slowly. The mixture was worked-up as above.
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