Simple and efficient preparation of ketones from morpholine amides

Synlett

Volumn , Issue 12, 1997, Pages 1414-1416

  Martin R ^a   Romea, P ^a   Tey, C ^a   Urpi F ^a   Vilarrasa, J ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002884392     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-1050     Document Type: Article

References (25)

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14. Amides 1-3 were prepared by reaction of acid chlorides with morpholine or pyrrolidine according to standard procedures.
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16. b) Yamaguchi, M.; Waseda, T.; Hirao, I. Chem. Lett. 1983, 35
17. Morpholine-derived amides afford better yields (75-80%) than pyrrolidine-derived amides (45-70%), when organolithium reagents are used as well.
18. Imamoto, T.; Kusumoto, T.; Tawarayama, Y.; Sugiura, Y.; Mita, T.; Hatanaka, Y.; Yokoyama, M. J. Org. Chem. 1984, 49, 3904.
19. 2).
20. For reviews, see: Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis; Wiley: New York, 1991.
21. Kocienski, P. J. Protecting Groups; Thieme: Stuttgart, 1994.
22. 3).
23. Ethereal solutions of EtLi were readily prepared from EtBr and Li. See: Brandsma, L.; Verkruijsse, H. Preparative Polar Organometallic Chemistry. 1; Springer-Verlag: Berlin, 1987. Commercially available 2 M THF solutions of EtMgCl, pur-chased from Aldrich, were used as received.
24. 2 for 12 h. The resulting suspension was filtered through a Celite® plug and evaporated in vacuo. The residue was purified by chromatography on silica gel (AcOEt) to afford (S)-3-ethyl-2,3-pentanediol (92 mg, 81%) as a colourless oil, which was submitted to GC analysis (column: Beta-DEX™ 120; fused silica capillary column, 30 m, 0.25 mm ID, 0.25 μm film thickness; Supelco) showing the material (3-ethyl-2,3-pentanediol) to be of ee > 96%.
25. 2 (see Ref. 6 for a related study). On the other hand, chelated species involving the oxygen atom of the morpholine ring are not detected.