2-aza-4-(alkoxycarbonyl)spiro[4,5]decan-3-one

Details 2-aza-4-(alkoxycarbonyl)spiro[4,5]decan-3-one 2-aza-4-(alkoxycarbonyl)spiro[4,5]decan-3-one

1989-08-30

1990-09-11

Berch, Mark L.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

558431, C07D20954, C07C25546, C07B 4306

Patent

active

049564730

ABSTRACT:
2-Aza-4-(alkoxycarbonyl)spiro[4,5]-decan-3-one and a process for the production of it, starting either from cyclohexylidene malonic acid esters or cyclohexylidene cyanoalkylates. The cyclohexylidene malonic acid ester is reacted with hydrocyanic acid in the presence of a catalytic amount of alkali cyanide or with a stoichiometric amount of alkali cyanide, in an alcohol, and subsequently treated with an acid. The resultant (1-cyanocyclohexyl) malonic acid dialkyl ester is converted by catalytic hydrogenation into the product. The cyclohexylidene cyanoalkylate is reacted with a stoichiometric amount of alkali cyanide, in an alcohol or with hydrocyanic acid in the presence of a catalytic amount of an alkali cyanide. The resultant (1-cyanocyclohexyl)-cyanoacetic acid alkyl ester is reacted in an alcohol in an acid to provide (1-cyanocyclohexyl) malonic acid dialkyl ester. The later ester is converted by catalytic hydrogenation into the product. Process of using the product for the production of 1-(aminomethyl)cyclohexane acetic acid by converting the product with HCl or sulfuric acid at an elevated temperature.

REFERENCES:
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patent: 4152326 (1979-05-01), Harterstein et al.
patent: 4855444 (1989-08-01), Wambach
Drugs of the Future, vol. 9, No. 6 (1984), pp 418 and 419.
Koelsch et al., JACS, vol. 66 (Nov. 1944), pp. 1883 & 1884.
Banerjee et al., J. Indian Chem. Soc., vol. LI (Jan. 1974), pp. 67-72.
Kemp et al., "Organic Chemistry" (1980), p. 38.

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