An efficient synthesis of morpholin-2-one derivatives using glycolaldehyde dimer by the Ugi multicomponent reaction

Organic Letters

Volumn 3, Issue 26, 2001, Pages 4149-4152

  Kim, Young Bae ^b   Choi, Eun Hee ^b   Keum, Gyochang ^a   Kang, Soon Bang ^a   Lee, Duck Hyung ^b   Koh, Hun Young ^a   Kim, Youseung ^a  

^a Korea Institute of Science and Technology   (South Korea)

^b Sogang University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001220302     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016716w     Document Type: Article

References (36)

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29. 2O (10 mL) and EtOAc (20 mL) were added to the residue, and the resulting aqueous solution was extracted with EtOAc (4 × 20 mL). The combined organic extracts were washed with brine (10 mL) and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by flash column chromatography on silica gel with a mixture of hexane and EtOAc (1:1 or 1:2) to give the corresponding morpholin-2-one-5-carboxamide 7.
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36. 3 was selected and attached to the tip of a glass fiber, transferred to a Bruker SMART diffractometer/CCD area detector, and centered under liquid nitrogen in the beam at 233(2) K. The structure was solved using the direct methods from the E-map. The remaining non-hydrogen atoms were located in an alternating series of least-squares cycles and difference Fourier maps. All non-hydrogen atoms were refined with anisotropic displacement coefficients. All hydrogen atoms were included in the structure factor calculation at idealized positions and were allowed to ride on the neighboring atoms with relative Isotropic displacement coefficients. The absolute configuration at C4 was derived from the known configuration of starting material cis-4-hydroxy-D-proline. Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication CCDC-163587 [(3S,5A)-7f] and CCDC-163588 [(4SJR.9R)-12h]. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB21EZ, UK (fax: (+44)1223-336-033; e-mail: deposit@ccdc.cam.ac.uk).