(2,3,4,5,6-pentafluorophenyl) ethenesulfonate

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 1-Ethylpiperidine hypophosphite (7.49 g, 41.8 mmol) were weighed into the reaction flask under an inert gas, and methylene chloride (38 ml) was added. The solution was cooled with ice-water, and 2,3,4,5,6-pentafluorophenyl 1-ethylenesulfonate (1.38 g, 5.02 mmol) [Org. Lett.; 2002; 4(15); 2549-2551] and tert-butyl 3-iodopiperidine-1-carboxylate (1.3 g, 4.18 mmol) was added at 0° C. Triethylborane solution (0.21 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. Stir for 5 min, the addition of triethylborane solution-compressed air was then repeated with the same amount. The reaction mixture was washed with water (20 ml), sodium bicarbonate solution (20 ml, saturated 50% diluted) and saturated sodium chloride solution (20 ml), dried over sodium sulfate and concentrated in vacuo. The crude product was purified by column chromatography (silica gel) with hexane/diethyl ether (3:1). Yield: 0.5 g (26%) was added was added at 0° C Stir for 5 min The reaction mixture was washed with water (20 ml), sodium bicarbonate solution (20 ml, saturated 50% diluted) and saturated sodium chloride solution (20 ml) dried over sodium sulfate concentrated in vacuo The crude product was purified by column chromatography (silica gel) with hexane/diethyl ether (3:1)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 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%) was added was added at 0° C The reaction mixture was washed with cooled water (10 ml) cooled saturated sodium bicarbonate soln (10 ml), dried over sodium sulfate 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%)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 1-Ethylpiperidine hypophosphite (30 g, 168 mmol) were weighed into the reaction flask under an inert gas, and methylene chloride (100 ml) was added. The solution was cooled with ice-water and 2,3,4,5,6-pentafluorophenyl 1-ethylenesulfonate (5.06 g, 18.5 mmol) [Org. Lett.; 2002; 4(15); 2549-2551] and (S)-tert-butyl 2-(iodomethyl)pyrrolidine-1-carboxylate (5.22 g, 16.8 mmol) was added at 10° C. Triethylborane solution (1.6 ml, 1 mol/l) was added and compressed air was then passed through the mixture for 5 sec. After stirring for min the addition of triethylborane solution-compressed air was repeated with the same amount. The cooling bath was removed, the mixture was stirred for 10 min and the reaction mixture was then washed with water (20 ml) and saturated sodium chloride solution (20 ml), dried over sodium sulfate and concentrated in vacuo. The crude product was purified by column chromatography (silica gel) with hexane/diethyl ether (2:1). Yield: 2.81 g (36%) was added was added at 10° C The cooling bath was removed the mixture was stirred for 10 min the reaction mixture was then washed with water (20 ml) and saturated sodium chloride solution (20 ml) dried over sodium sulfate concentrated in vacuo The crude product was purified by column chromatography (silica gel) with hexane/diethyl ether (2:1)