Triethylborane → HCID 59367796, compound

Participants

Reaction Steps

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%)

Provenance & Evidence