Methyl iodide → Ethyl 1-methyl-5-oxoprolinate

HRID 2238517

Reaktionsgleichung

Reaktionsgleichung von HRID 2238517
[CH2:1]([O:3][C:4](=[O:11])[C@H:5]1[CH2:9][CH2:8][C:7](=[O:10])[NH:6]1)[CH3:2].[CH3:12]I.[H-].[Na+].[Cl-].[NH4+]>O1CCCC1>[CH3:12][N:6]1[C:7](=[O:10])[CH2:8][CH2:9][C@H:5]1[C:4]([O:3][CH2:1][CH3:2])=[O:11]

Komponenten

6

Edukt 4

HCID 6328Methyl iodideHCID 24758Sodium hydride2×HCID 25517Ammonium ChlorideHCID 643508ethyl (2R)-5-oxopyrrolidine-2-carboxylate

Produkt 1

HCID 15225832Ethyl 1-methyl-5-oxoprolinateAusbeute 6,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

D-pyroglutamic acid ethyl ester (4.0 g, 25.5 mmol) was dissolved in tetrahydrofuran (25 ml) and cooled to 0° C. Methyl iodide (1.66 ml, 26.7 mmol) was added and stirring continued for 10 minutes under argon at 0° C. Sodium hydride (60% in oil, 1.6 g, 26.7 mmol) was then added portionwise (allowing each portion to react). After addition of all the sodium hydride the mixture was allowed to warm to room temperature and stirred overnight under argon. The mixture was then treated with saturated aqueous ammonium chloride solution (˜15 ml) and stirred for 4 hrs. The organic layer was separated and the aqueous layer was extracted with more dichloromethane. The combined organic layers were dried over magnesium sulphate and then concentrated to a dark oil. This was purified by flash silica column chromatography, eluting with a 0-75% gradient of ethyl acetate in hexane, to give ethyl 1-methyl-5-oxoprolinate as a colourless oil (0.27 g) which was used in the next step without further purification.

Aufarbeitung

  1. customto react)
  2. temperatureto warm to room temperature
  3. stirringstirred overnight under argon
  4. stirringstirred for 4 hrs
  5. customThe organic layer was separated
  6. extractionthe aqueous layer was extracted with more dichloromethane
  7. dry with materialThe combined organic layers were dried over magnesium sulphate
  8. concentrationconcentrated to a dark oil
  9. customThis was purified by flash silica column chromatography
  10. washeluting with a 0-75% gradient of ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-0843eb59f3364f3eae31d58cd60dc46d
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07718693B2

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