Ammonium Chloride → methyl 2-hydroxy-2-(1-methyl-1H-indol-3-yl)acetate
Reaktionsgleichung
[Li+].CC([N-]C(C)C)C.[CH3:9][N:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([CH2:19][C:20]([O:22][CH3:23])=[O:21])=[CH:11]1.CC1(C)[C@@]23[C@@]4(ON4S(=O)(=[O:32])C2)C[C@H]1CC3.[Cl-].[NH4+]>O1CCCC1>[OH:32][CH:19]([C:12]1[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:10]([CH3:9])[CH:11]=1)[C:20]([O:22][CH3:23])=[O:21]Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- -78 °C
Versuchsvorschrift
To a solution of 2.87 millimole of LDA in 5 mL of dry tetrahydrofuran at -78° C. was added dropwise a solution of 0.53 g of methyl 2-(1-methyl-3-indolyl)acetate in 5 mL of dry tetrahyrofruan. The mixture was stirred for 30 minutes at -78° C., and then 0.9 g of (+)-(2R,8aS)-(camphorsulfonyl)oxaziridine was added. The mixture was warmed to room temperature and stirred for 2 hours. Then the mixture was poured into a solution of saturated aqueous ammonium chloride, and then extracted with diethyl ether. The ether extract was dried with magnesium sulfate and concentrated by evaporation. The residue was subjected to silica gel chromatography using a developing solution of dichloromethane/ethyl acetate (98:2 by volume) to give 0.38 g of an oily product.
Aufarbeitung
- temperatureThe mixture was warmed to room temperature
- stirringstirred for 2 hours
- extractionextracted with diethyl ether
- extractionThe ether extract
- dry with materialwas dried with magnesium sulfate
- concentrationconcentrated by evaporation
Quellen und Nachweise
- ORD-Eintrag
- ord-bc29dd460ed14424aadf395cd905b66a
- Quelldatensatz
- uspto-grants-1998_05
- Patentnummer
- US05747236
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