Preparation of erythio-.alpha.piperid-2-yl-2,8-bis-trifluoro-met

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

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C07D40106

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043272150

ABSTRACT:
The present invention relates to a simplified process, which avoids organo-lithium intermediates, for the preparation of erythro-.alpha.-piperid-2-yl-2,8-bis-(trifluoromethyl)-quinolin-4-yl-metha nol, wherein 2,8-bis-(trifluoromethyl)-quinoline-4-carboxylic acid or a salt thereof is reacted with a pyrid-2-yl-magnesium halide to give pyrid-2-yl-2,8-bis-(trifluoromethyl)-quinolin-4-yl ketone in the manner of a Grignard reaction, and this product is hydrogenated, in a conventional manner, to give erythro-.alpha.-piperid-2-yl-2,8-bis-(trifluoromethyl)-quinolin-4-yl-metha nol.

REFERENCES:
Grignard, "Comptes Rendus", Bd. 138,pp. 152-154 (1904).
Org. Reactions, vol. 18, pp. 4 & 5 (1970).
Barton et al., Comp. Org. Chem., vol. 2, pp. 645 & 646 (1979).
Krauch et al., Reac. der Org. Chem., Huthia-Verlag, Heidelberg, pp. 262 & 263 (1976).
Ohnmacht et al., J. Med. Chem, 14, pp. 926-928 (1971).
Maginnity et al., JACS 73, pp. 3579 & 3780 (1951).
Ludwall et al., JACS, 53, pp. 318-319 (1931).
Org. Syn., vol. I, 2nd Ed., pp. 327-330, Wiley, N.Y., NY (1941).
Gilman, Org. Chem., p. 417, vol. 5, Wiley & Sons, N.Y., N.Y. (1938).

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