1-Methylimidazole → [4-(1-Methyl-1H-imidazol-2-yl)-4-oxobutyl]carbamic acid 1,1-dimethylethyl ester

Temperature

-70 °C

N-methylimidazole (0.83 g, 10.1 mmol) was dissolved in anhydrous tetrahydrofuran (30 ml) and the solution cooled to −70° C. n-Butyllithium (2.29M, 3.48 ml, 10.1 mmol) was added dropwise and the solution stirred for 0.5hat −70° C. 1,1-Dimethylethyl [4-(methoxymethylamino)-4-oxobutyl]-carbamate (1.24 g, 5.03 mmol) as a solution in tetrahydrofuran (50 ml) was added dropwise and the resultant solution stirred at −70° C. for 1 h. The cooling bath was removed and the reaction mixture allowed to warm to 0° C. The reaction was quenched with saturated aqueous ammonium chloride solution (30 ml) and extracted with ethyl acetate (3×70 ml). The combined extracts were washed with water (2×20 ml), dried (magnesium sulphate) and evaporated. The residue was eluted down a flash chromatography column eluting with hexane:ethyl acetate (3:1) to afford the sub-title compound as a pale straw-coloured oil (0.82 g, 61%);

1. additionwas added dropwise
2. customThe cooling bath was removed
3. temperatureto warm to 0° C
4. customThe reaction was quenched with saturated aqueous ammonium chloride solution (30 ml)
5. extractionextracted with ethyl acetate (3×70 ml)
6. washThe combined extracts were washed with water (2×20 ml)
7. dry with materialdried (magnesium sulphate)
8. customevaporated
9. washThe residue was eluted down a flash chromatography column
10. washeluting with hexane:ethyl acetate (3:1)

ORD record

ord-18bf273c8eb64bc588dbab0555aeab56

Source dataset

uspto-grants-2004_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06743939B2