Toluene → 4-propyl-1-(1H-pyrrol-1-ylmethyl)pyrrolidin-2-one

18-Crown-6 (0.158 g, 0.2 eq, 0.6 mmol) is dissolved in absolute ether (20 ml). A 1.7 M solution of potassium tert-amylate in toluene (1.93 ml, 1.1 eq, 3.28 mmol) is added dropwise in a flow of argon. The reaction mixture is stirred for 15 min at room temperature. Pyrrole (0.2 g, 1 eq, 2.98 mmol) is added. The reaction mixture is cooled to −15° C., and a solution of 1-(chloromethyl)-4-propylpyrrolidin-2-one x63 (0.603 g, 1.15 eq, 3.43 mmol) in absolute ether (5 ml) is added dropwise. The resulting solution is stirred for 16 h at 20° C. The contents of the flask are partitioned between 10 ml of water and 30 ml of ethyl acetate. The organic layer is separated. The aqueous one is subjected to additional extraction with ethyl acetate (2×20 ml). The combined extracts are dried with anhydrous Na2SO4 and evaporated. Purification by chromatography on silicagel (dichloromethane/acetone) afford 0.091 g of 4-propyl-1-(1H-pyrrol-1-ylmethyl)pyrrolidin-2-one x264.

1. temperatureThe reaction mixture is cooled to −15° C.
2. stirringThe resulting solution is stirred for 16 h at 20° C
3. customThe contents of the flask are partitioned between 10 ml of water and 30 ml of ethyl acetate
4. customThe organic layer is separated
5. extractionThe aqueous one is subjected to additional extraction with ethyl acetate (2×20 ml)
6. dry with materialThe combined extracts are dried with anhydrous Na2SO4
7. customevaporated
8. customPurification by chromatography on silicagel (dichloromethane/acetone)

ORD record

ord-be89b50fdeaa4ec1ad319ea81d1c015b

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08586623B2