Triethylborane → Perfluorophenyl 3-(1-(4-methoxy-2,6-dimethylphenylsulfonyl)piperidin-2-yl)propane-1-sulfonate

1-Ethylpiperidine hypophosphite (1.184 g, 6.614 mmol) were weighed into the reaction flask under an inert gas, and methylene chloride (10 ml) was added. The solution was cooled with ice-water, and 2,3,4,5,6-pentafluorophenyl 1-ethylenesulfonate (0.218 g, 0.794 mmol) [Org. Lett.; 2002; 4(15); 2549-2551] and 2-(iodomethyl)-1-(4-methoxy-2,6-dimethylphenylsulfonyl)piperidine (0.28 g, 0.661 mmol) was added at 0° C. Triethylborane solution (0.03 ml, 1 mol/l) was added to the reaction mixture and compressed air was then passed through the mixture for 10 sec. After stirring for 5 min the addition of triethylborane solution-compressed air was repeated with the same amount. After thin layer chromatography control, the addition of triethylborane soln.-compressed air was repeated again with the same amount. The reaction mixture was washed with cooled water (10 ml) and cooled saturated sodium bicarbonate soln. (10 ml), dried over sodium sulfate and concentrated in vacuo. The crude product was purified by column chromatography (silica gel) with hexane/diethyl ether/methylene chloride (6:1:1) Yield: 50 mg (13%)

1. additionwas added
2. additionwas added at 0° C
3. washThe reaction mixture was washed with cooled water (10 ml)
4. temperaturecooled saturated sodium bicarbonate soln
5. dry with material(10 ml), dried over sodium sulfate
6. concentrationconcentrated in vacuo
7. customThe crude product was purified by column chromatography (silica gel) with hexane/diethyl ether/methylene chloride (6:1:1) Yield: 50 mg (13%)

ORDレコード

ord-9123c3927a3b457b922acaa2905f4b69

出典データセット

uspto-grants-2012_02

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08119805B2