Method for the preparation of derivatives of spiro (4,5)-decane

Details Method for the preparation of derivatives of spiro (4,5)-decane Method for the preparation of derivatives of spiro (4,5)-decane

1975-02-11

1977-06-07

Todd, G. Thomas

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

260270PD, 26029358, 26029366, 26029376, 26029378, 2602938, 26029382, 424267, C07D49810

Patent

active

040283518

ABSTRACT:
Derivatives of spiro-(4,5)-decane, are prepared from an N-substituted-4-piperidone according to a modification of the Reformatsky reaction. The N-substituted-4-piperidone is reacted in an appropriate solvent or solvent mixture with an alpha halogen ester in the presence of activated zinc. The obtained beta-hydroxy ester is reacted with an excess of hydrazine, the resultant compound being a beta hydroxy hydrazide. The latter is subjected to a Curtius transposition with nitrous acid in excess.

REFERENCES:
patent: 3655673 (1972-04-01), Maillard
patent: 3721675 (1973-03-01), Maillard
Shapiro, J. Org. Chem. 15, 1027-1036, (1950).
Grob et al., Helv. Chim. Acta 41, 1184-1190, (1958).

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