(+)-Trimethyl 3-nitro-2-(2,4,6-trimethoxyphenyl)propane-1,1,3-tricarboxylate → (+)-Dimethyl 5-oxo-3-(2,4,6-trimethoxyphenyl)pyrrolidine-2,4-dicarboxylate

関与物質

反応手順

To a 1 L pressure reactor, tetrahydrofuran (100 mL) and Raney nickel (20 g) was added followed by the addition of a solution of (+)-trimethyl 3-nitro-2-(2,4,6-trimethoxyphenyl)propane-1,1,3-tricarboxylate (32 g, 0.074 mol) in tetrahydrofuran (300 mL). Under stirring, the reactor was purged three times with nitrogen followed by hydrogen. The reaction mixture was stirred overnight under a hydrogen pressure of 80 psi. At the end of the reaction, Raney nickel was filtered off and washed with tetrahydrofuran (150 mL) under nitrogen. The organic layer was concentrated under reduced pressure to yield a white solid. 1H NMR revealed the presence of a mixture of isomers. The mixture of cis and trans isomers was obtained in a yield of 25 g (91.32%). A small portion of reaction mixture was purified by column chromatography using 5% methanol in chloroform as eluting agent to separate the isomers and one of the separated isomers was found to be identical to the isomer obtained by reduction using stannous chloride, confirmed by 1H NMR, mass spectra and HPLC.

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