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

HRID 1643460Notes

Reaction equation

HRID 1643460 reaction equation
[PH2](O)=O.C(N1CCCCC1)C.[CH2:12]=[CH:13][S:14]([O:17][C:18]1[C:23]([F:24])=[C:22]([F:25])[C:21]([F:26])=[C:20]([F:27])[C:19]=1[F:28])(=[O:16])=[O:15].I[CH2:30][CH:31]1[CH2:36][CH2:35][CH2:34][CH2:33][N:32]1[S:37]([C:40]1[C:45]([CH3:46])=[CH:44][C:43]([O:47][CH3:48])=[CH:42][C:41]=1[CH3:49])(=[O:39])=[O:38].C(B(CC)CC)C>C(Cl)Cl>[CH3:48][O:47][C:43]1[CH:44]=[C:45]([CH3:46])[C:40]([S:37]([N:32]2[CH2:33][CH2:34][CH2:35][CH2:36][CH:31]2[CH2:30][CH2:12][CH2:13][S:14]([O:17][C:18]2[C:19]([F:28])=[C:20]([F:27])[C:21]([F:26])=[C:22]([F:25])[C:23]=2[F:24])(=[O:16])=[O:15])(=[O:38])=[O:39])=[C:41]([CH3:49])[CH:42]=1

Participants

6

Reactant 4

HCID 7357Triethylborane3×HCID 2763990Pentafluorophenyl vinylsulfonateHCID 593677522-(Iodomethyl)-1-(4-methoxy-2,6-dimethylphenylsulfonyl)piperidineHCID 178462538HCID 178462538, compound

Product 1

HCID 59367793Perfluorophenyl 3-(1-(4-methoxy-2,6-dimethylphenylsulfonyl)piperidin-2-yl)propane-1-sulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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%)

Workup

  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%)

Sources & evidence

ORD record
ord-9123c3927a3b457b922acaa2905f4b69
Source dataset
uspto-grants-2012_02
Patent number
US08119805B2

Reaction notes

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