Ammonium Chloride → HCID 86759699, compound

3-Bromofuran (5.88 g, 40 mmol) was dissolved in anhydrous tetrahydrofuran (60 ml) and the solution cooled to −78° C. n-Butyllithium (2.29M, 17.5 ml, 40 mmol) was added dropwise and the solution stirred for 1 h at −78° C. [3-(Methoxymethylamino)-3-oxopropyl]carbamic acid, 1,1-dimethylethyl ester as a solution in tetrahydrofuran (40 ml) was added dropwise over 1 h. The solution was stirred overnight whilst allowing to warm to room temperature. Aqueous saturated ammonium chloride solution (30 ml) was added and the mixture extracted with ethyl acetate (3×70 ml). The combined organic extracts were washed with water (3×30 ml), dried (sodium sulphate) and evaporated in vacuo. The residue was chromatographed on flash silica, eluting with hexane:ethyl acetate (7:3), to afford the title compound as a pale yellow solid (3.03 g, 63%).

1. additionwas added dropwise
2. additionwas added dropwise over 1 h
3. extractionthe mixture extracted with ethyl acetate (3×70 ml)
4. washThe combined organic extracts were washed with water (3×30 ml)
5. dry with materialdried (sodium sulphate)
6. customevaporated in vacuo
7. customThe residue was chromatographed on flash silica
8. washeluting with hexane:ethyl acetate (7:3)

ORD record

ord-e19912ffbc774885909b91c6328873a1

Source dataset

uspto-grants-2005_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06887871B2