Methyl iodide → Ethyl 1-methyl-5-oxoprolinate

온도

0 °C

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.

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

ORD 기록

ord-282b0bc8db9d4fe182eadf36aa3eaf9b

출처 데이터셋

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08048907B2