Undec-4-ene → Diethyl 2-oxopyrrolidine-5,5-dicarboxylate

2(b) 314 μl of 1,8-diaza[5.4.0]-7-undecene were added to a solution of 620 mg of diethyl 2-(3-bromopropionamido)malonate (prepared as described above) dissolved in methylene chloride, and the mixture was stirred at room temperature for 3 hours. At the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure, poured into water and then extracted with diethyl ether. The extract was washed with 5% w/v aqueous hydrochloric acid, with a 5% w/v aqueous solution of sodium bicarbonate and with water, in that order, and dried over anhydrous magnesium sulfate. The solvent was then removed by distillation under reduced pressure, to give a crude product. This was purified by column chromatography through silica gel, eluted with a 2:1 by volume mixture of cyclohexane and ethyl acetate, to give 171 mg of diethyl 2-oxopyrrolidine-5,5-dicarboxylate.

1. concentrationAt the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure
2. additionpoured into water
3. extractionextracted with diethyl ether
4. washThe extract was washed with 5% w/v aqueous hydrochloric acid, with a 5% w/v aqueous solution of sodium bicarbonate and with water, in that order
5. dry with materialdried over anhydrous magnesium sulfate
6. customThe solvent was then removed by distillation under reduced pressure
7. customto give a crude product
8. customThis was purified by column chromatography through silica gel
9. washeluted with a 2:1 by volume mixture of cyclohexane and ethyl acetate

ORDレコード

ord-5e6e85e2d9d8426d99779a089a22f9f3

出典データセット

uspto-grants-1996_06

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US05527905