反应详情

Add cesium carbonate (1.13 g, 3.46 mmol, 1.50 equivalents) and copper iodide (44 mg, 0.23 mmol, 0.10 equivalents) to a stirred solution of 4-[1-(3-bromo-5-methoxymethyl-thiophen-2-yl)-1-hydroxyimino-methyl]-piperidine-1-carboxylic acid tert-butyl ester (1.00 g, 2.31 mmol, 1.00 equivalents) in 2-methoxy ethanol (23.30 mL). Stir the resulting mixture at room temperature overnight or up to 3 days and filter through celite. Evaporate the filtrate, partition the residue between ethyl acetate (70 mL) and water (23 mL) and separate. Extract the aqueous layer with ethyl acetate (3×70 mL), combine the organic layers, dry over magnesium sulfate, filter and evaporate. Purify the residue via flash column chromatography eluting with a mixture of hexane:ethyl acetate (4:1) to yield the desired product as a yellow oil. LC/MS (ESI), m/e 375 (MNa+), retention time 1.98 minutes. Condition II.

1. waitup to 3 days
2. filtrationfilter through celite
3. customEvaporate the filtrate
4. custompartition the residue between ethyl acetate (70 mL) and water (23 mL)
5. customseparate
6. extractionExtract the aqueous layer with ethyl acetate (3×70 mL)
7. dry with materialdry over magnesium sulfate
8. filtrationfilter
9. customevaporate
10. customPurify the residue via flash column chromatography
11. washeluting with a mixture of hexane:ethyl acetate (4:1)