Reaktionsgleichung
C1C2N(C(=O)CC2)C(=O)C1.O[N:12]=[C:13]([CH2:19][CH2:20][C:21]([OH:23])=[O:22])[CH2:14][CH2:15][C:16](O)=[O:17].[H][H]>[Rh]>[O:17]=[C:16]1[NH:12][CH:13]([CH2:19][CH2:20][C:21]([OH:23])=[O:22])[CH2:14][CH2:15]1Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
In a process for preparing dihydro-1H-pyrrolizine-3,5(2H, 6H)-dione comprising the steps of catalytically hydrogenating an ester of 4-(hydroxyimino)heptanedioic acid and subsequently cyclizing the resulting product to dihydro-1H-pyrrolizine-3,5(2H,6H)-dione, the improvement comprises reacting an alcoholic solution of a mono(lower alkyl) ester of 4-(hydroxyimino)heptanedioic acid, wherein lower alkyl comprises from one to three carbon atoms, with hydrogen gas at a temperature of about 60° C. in the presence of rhodium/alumina catalyst and a tertiary lower alkyl amine, wherein said lower alkyl amine comprises from three to nine carbon atoms, to produce 5-oxo-2-pyrrolidinepropanoic acid; and thereafter heating said 5-oxo-2-pyrrolidinepropanoic acid in the presence of a cyclizing agent selected from acetic anhydride, 2,2,6-trimethyl-1,3-dioxen-4-one, and diketene at a temperature of about 90° C. to produce dihydro-1H-pyrrolizine-3,5(2H,6H)-dione.
Quellen und Nachweise
- ORD-Eintrag
- ord-72f5e6ab7c96414883912fbea769defb
- Quelldatensatz
- uspto-grants-1987_05
- Patentnummer
- US04663464
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