Methyl iodide → (2R,4R)-4-Methoxy-1-trityl-pyrrolidine-2-carboxylic acid methyl ester
Reaktionsgleichung
[CH3:1][O:2][C:3]([C@H:5]1[CH2:9][C@@H:8]([OH:10])[CH2:7][N:6]1[C:11]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:4].CI.[H-].[Na+].[CH3:34]COC(C)=O>CN(C=O)C.C1COCC1>[CH3:1][O:2][C:3]([C@H:5]1[CH2:9][C@@H:8]([O:10][CH3:34])[CH2:7][N:6]1[C:11]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)=[O:4]Komponenten
7
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
Into a solution of 2 (5.71 g, 14.7 mmol) in anhydrous DMF (20 mL) and anhydrous THF (20 mL) was added MeI (3.67 mL, 58.9 mmol). The solution was cooled to 0° C. in an ice bath and NaH (0.766 g, 19.2 mmol) was added in one portion. The mixture was stirred at RT for 26 h before adding EtOAc and washing sequentially with water and brine. The organic layer was dried over MgSO4 and concentrated under reduced pressure. Purification of the crude material by flash chromatography revealed 3 (4.67 g, 79%) as a white solid.
Aufarbeitung
- washwashing sequentially with water and brine
- dry with materialThe organic layer was dried over MgSO4
- concentrationconcentrated under reduced pressure
- customPurification of the crude material by flash chromatography
Quellen und Nachweise
- ORD-Eintrag
- ord-ece8b149bdbe49069cab0d853ee02992
- Quelldatensatz
- uspto-grants-2008_08
- Patentnummer
- US07407972B2
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