Abstract
A method to reduce the nitro moiety in dimethyl 4-nitro-4-[1-[2(methoxycarbonyl)ethyl]]heptanedioate using a T-1 Raney nickel catalyst in an acidic environment is reported. The method avoids facile lactam formation.
Highlights
Prevention of facile lactam formation upon reduction of the nitro moiety in dimethyl 4-nitro-4-[1[2-(methoxycarbonyl)ethyl]]heptanedioate (1) [1] to yield dimethyl 4-amino-4-[2-(methoxycarbonyl)ethyl]-heptanedioate (2) has proved problematic [2]
Lactam formation occurred if the reduction was proceeding too slowly or if the amine salt was allowed to remain under reaction conditions overnight
After the complex was removed by filtration and the product concentrated in vacuo for at least 24 hours, the amine salt was redissolved in methylene chloride and filtered to remove additional nickel–dimethyl glyoxime complex and afforded 2 as a pale yellow gel (80.1%)
Summary
Prevention of facile lactam formation upon reduction of the nitro moiety in dimethyl 4-nitro-4-[1[2-(methoxycarbonyl)ethyl]]heptanedioate (1) [1] to yield dimethyl 4-amino-4-[2-(methoxycarbonyl)ethyl]-heptanedioate (2) has proved problematic [2]. Lactam (3) formation was prevented by replacing the methyl ester termini with t-butylesters [2,3]. A method has been developed that accomplishes this by the formation of the amine salt.
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