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Synlett 1990; 1990(11): 669-670
DOI: 10.1055/s-1990-21204
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Preparation of N-Demethyl and N-Alkyl Analogs of L-Rhodosamine

J. P. Gesson* , J. C. Jacquesy, M. Mondon
  • *Laboratoire de Chimie XII, URA 489, 40 Avenue du Recteur Pineau, F-86022 Poitiers, France
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Publication Date:
08 March 2002 (online)

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Iron(II) chloride catalyzed decomposition of the N-oxide of methyl-α-L-rhodosaminide (methyl 2,3,6-trideoxy-3-dimethylamino)-α-L-lyxo-hexopyranoside N-oxide) affords an oxazolidine [(3aS,4S,6R,7aS)-6-methoxy-1,4-dimethyl-1,3a,4,6,7, 7a-hexahydro-2H-pyrano[4,3-d]oxazole] through addition of the C-4 hydroxyl group to the intermediate imminium ion. The same reaction has also been observed for N-methylephedrine. Subsequent condensation of the oxazolidine with Grignard reagents leads to N-alkyl derivatives of the title compound.

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