n-Butyl lithium → 1-(Styrenesulphonyl)-2-oxo-5-methoxy pyrrolidine
Reaktionsgleichung
[CH3:1][O:2][CH:3]1[NH:7][C:6](=[O:8])[CH2:5][CH2:4]1.[Li+].CCC[CH2-].[CH:14]([S:22](Cl)(=[O:24])=[O:23])=[CH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>O1CCCC1.CCCCCC>[CH:14]([S:22]([N:7]1[CH:3]([O:2][CH3:1])[CH2:4][CH2:5][C:6]1=[O:8])(=[O:24])=[O:23])=[CH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1Komponenten
Reaktionsbedingungen
- Temperatur
- -20 °C
Versuchsvorschrift
3.29 g of 5-methoxy-2-oxo pyrrolidine (SYNTHESIS 4, 315-17 (1980)) is dissolved in 100 cm3 of anhydrous tetrahydrofuran. After cooling to -20° C. 17.86 cm3 of a 1.6M solution of N-butyllithium in hexane is a while keeping the temperature at about -30° C. The mixture is agitated for 30 minutes at -35° to -30° C., then a solution of 5.80 g of styrenesulphonyl chloride (CA 47, 3262c, 1953) in 14 cm3 of anhydrous tetrahydrofuran is added slowly. After allowing this to return to ambient temperature, the solvent is evaporated under reduced pressure, and the residue is chromatographed on silica gel, eluting with a mixture of ethyl acetate and n-hexane (1--). The product obtained is crystallized from isopropanol, and 3 g of the expected product is obtained. m.p. 98°-99° C.
Aufarbeitung
- customat about -30° C
- customthis to return to ambient temperature
- customthe solvent is evaporated under reduced pressure
- customthe residue is chromatographed on silica gel
- washeluting with a mixture of ethyl acetate and n-hexane (1--)
- customThe product obtained
- customis crystallized from isopropanol
Quellen und Nachweise
- ORD-Eintrag
- ord-04fdda8624d1458cb1929f149297f82c
- Quelldatensatz
- uspto-grants-1989_03
- Patentnummer
- US04810722
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