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OPPI BRIEFS

A PRACTICAL LARGE-SCALE PREPARATION OF 5'-BROMOSPIRO(CYCLOHEXANE-1,3-[3H]INDOL)-2'(1'H)-ONE

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Pages 283-285 | Received 30 Mar 1905, Published online: 06 Feb 2009

References

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  • Moore , R. F. and Plant , S. G. P. 1951 . J. Chem. Soc. , : 3475 Other methods are less suitable for scale-up
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  • TMEDA, a complexing agent used in the Kende procedure, was later replaced with LiCl which simplified the work-up. Also, 1,5-dibromopentane, 1,5-ditosylpentane, and a 1:1 mixture of 1,5-dibromo- and 1,5-diiodopentane were tried with no apparent improvement in the yield and the purification procedure.
  • Sun , L. , Tran , N. , Tang , F. , App , H. , Hirth , P. , McMahon , G. and Tang , C. 1998 . J. Med. Chem. , 41 : 2588 We found this method impractical for a large-scale preparation
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  • Alkylation of oxindole under conditions described in Ref. 8 required extensive chromatographic purification.

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