Reaktionsgleichung
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:29][O:30][C:31]([C@@H:33]1[CH2:37][C:36](=[O:38])[N:35]([C:39]2[CH:44]=[CH:43][C:42](O)=[CH:41][CH:40]=2)[CH2:34]1)=[O:32].N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[CH3:29][O:30][C:31]([C@@H:33]1[CH2:37][C:36](=[O:38])[N:35]([C:39]2[CH:44]=[CH:43][C:42]([O:7][CH2:6][C:5]3[CH:8]=[CH:9][C:2]([F:1])=[CH:3][CH:4]=3)=[CH:41][CH:40]=2)[CH2:34]1)=[O:32]Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
A solution of 4.3 mmol of 4-fluoro-benzylalcohol and 4.7 mmol of triphenylphosphine in 7 ml of tetrahydrofuran was added dropwise at 0° C. to a solution of 4.7 mmol of (R)-1-(4-hydroxyphenyl)-5-oxo-pyrrolidine-3-carboxylic acid methyl ester [Example 2 a) or 8 a)] and 4.7 mmol of diisopropyl azodicarboxylate in 11 ml of tetrahydrofuran. The mixture was left to warm to RT and stirring was continued for 18 hours. After addition of 2 g of silica gel, the reaction mixture was evaporated under reduced pressure. The material obtained was chromatographed on silica gel using first a 2:1-mixture, then a 1:1-mixture of heptane and ethyl acetate as the eluent, yielding (R)-1-[4-(4-fluoro-benzyloxy)-phenyl]-5-oxo-pyrrolidine-3-carboxylic acid methyl ester as a white solid; MS: m/e=344 (M+H)+.
Aufarbeitung
- waitThe mixture was left
- additionAfter addition of 2 g of silica gel
- customthe reaction mixture was evaporated under reduced pressure
- customThe material obtained
- customwas chromatographed on silica gel using first a 2
Quellen und Nachweise
- ORD-Eintrag
- ord-40ba49ec3aa64e9299fff1a5e8364e49
- Quelldatensatz
- uspto-grants-2006_12
- Patentnummer
- US07148362B2
Verknüpfte Notizen
Wird geladen…