Methyl iodide → HCID 67461073, compound

Temperature

0 °C

1,1-dimethylethyl 3-methyl-5-oxoprolinate (0.79 g, 3.96 mmol) was dissolved in tetrahydrofuran (8 ml) and treated with methyl iodide (0.27 ml, 4.36 mmol). The mixture was then cooled to 0° C. and treated portion-wise with sodium hydride (60% in oil, 0.170 g, 4.36 mmol). The mixture ceased bubbling after 30 minutes at 0° C. and was then allowed to warm to room temperature and stirred overnight. The mixture was quenched by addition of saturated aqueous ammonium chloride solution (10 ml) and the organic layer was separated and put aside. The aqueous layer was extracted with dichloromethane (3×20 ml) and the combined extracts were dried using a hydrophobic frit. All of the organic fractions (including that put aside earlier) were combined and evaporated to give crude 1,1-dimethylethyl 1,3-dimethyl-5-oxoprolinate (0.770 g) as a yellow gum which was used without further purification.

1. customThe mixture ceased bubbling after 30 minutes at 0° C.
2. temperatureto warm to room temperature
3. customThe mixture was quenched by addition of saturated aqueous ammonium chloride solution (10 ml)
4. customthe organic layer was separated
5. extractionThe aqueous layer was extracted with dichloromethane (3×20 ml)
6. customthe combined extracts were dried
7. customevaporated

ORD record

ord-d82ef65701d1445e945a3a1257de889b

Source dataset

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08048907B2