FIELD: chemistry.
SUBSTANCE: invention refers to a method for producing diethyl[3-methyl-(1S)-(nitromethyl)butyl]malonate of formula I by enanthioselective attachment of diethylmalonate to 4-methyl-1-nitropent-1-ene in accordance with the scheme below. A reaction of diethylmalonate and 4-methyl-1-nitropent-1-ene is carried out in the presence of a catalyst system representing a nickel chloride hexahydrate solution, (S,S)-N,N'-dibenzylcyclohexane-1,2-diamine and triethylamine in molar ratio 1:1:1 in methanol. Preferentially, the catalyst system components are used in ratio 0.05-1 mole % in relation to 4-methyl-1-nitropent-1-ene. The method enables producing diethyl[3-methyl-(1S)-(nitromethyl)butyl]malonate with an enanthiomeric excess of 96.6-97.2% with the use of the catalyst system generated from nickel chloride hexahydrate, (S,S)-N,N'-dibenzylcyclohexane-1,2-diamine and triethylamine, avoiding the stage of individual complex recovery.
EFFECT: considerable cost-cutting and simplification of the technological process.
2 cl, 5 ex
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Authors
Dates
2015-07-10—Published
2014-02-12—Filed