Triethylamine → HCID 86670531, compound

HRID 1808738Notes

Reaction equation

HRID 1808738 reaction equation
FC(F)(F)C([O-])=[O:4].[F:8][C:9]([F:27])([F:26])[C:10]1[CH:15]=[CH:14][C:13]([S:16]([O:19][CH:20]2[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)(=[O:18])=[O:17])=[CH:12][CH:11]=1.[C:28]([S:32](Cl)=[O:33])([CH3:31])([CH3:30])[CH3:29].C(N(CC)CC)C.ClC1C=CC=C(C(OO)=O)C=1>C(OCC)C.O1CCCC1>[F:27][C:9]([F:8])([F:26])[C:10]1[CH:11]=[CH:12][C:13]([S:16]([O:19][CH:20]2[CH2:25][CH2:24][N:23]([S:32]([C:28]([CH3:31])([CH3:30])[CH3:29])(=[O:33])=[O:4])[CH2:22][CH2:21]2)(=[O:18])=[O:17])=[CH:14][CH:15]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 70297m-Chloroperbenzoic acidHCID 84468TrifluoroacetateHCID 46868612-Methylpropane-2-sulfinyl chlorideHCID 86670530HCID 86670530, compound

Product 1

HCID 86670531HCID 86670531, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a tetrahydrofuran (20 mL) solution of the trifluoroacetate salt of piperidin-4-yl 4-(trifluoromethyl)benzenesulfonate (800 mg, 1.97 mmol) at −78° C. was added tert-butylsulfinyl chloride (209 μL, 2.20 mmol). The reaction mixture was stirred for 10 minutes at −78° C. before triethylamine (1.10 mL, 7.88 mmol) was added. It was then stirred for another 2 hours at −78° C. Diethyl ether (50 mL) was added to the reaction mixture, and the combined organic layers were washed with 1 M hydrochloric acid (30 mL), water (30 mL), brine (30 mL), dried (sodium sulfate), filtered and concentrated in vacuo. The resulting oil was dissolved in dichloromethane (20 mL), cooled to 0° C., and m-chloroperbenzoic acid (374 mg, 2.17 mmol) was added to the solution. The ice-bath was removed, and the mixture was stirred at room temperature for 45 minutes. The reaction mixture was washed with saturated sodium bicarbonate (40 mL), water (40 mL), brine (40 mL), dried (magnesium sulfate), filtered and concentrated in vacuo. Chromatography over silica gel, eluting with hexanes/ethyl acetate, afforded the title compound.

Workup

  1. additionwas added
  2. washthe combined organic layers were washed with 1 M hydrochloric acid (30 mL), water (30 mL), brine (30 mL)
  3. dry with materialdried (sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. dissolutionThe resulting oil was dissolved in dichloromethane (20 mL)
  7. temperaturecooled to 0° C.
  8. customThe ice-bath was removed
  9. stirringthe mixture was stirred at room temperature for 45 minutes
  10. washThe reaction mixture was washed with saturated sodium bicarbonate (40 mL), water (40 mL), brine (40 mL)
  11. dry with materialdried (magnesium sulfate)
  12. filtrationfiltered
  13. concentrationconcentrated in vacuo
  14. washChromatography over silica gel, eluting with hexanes/ethyl acetate

Sources & evidence

ORD record
ord-e36d2fabb1d14287aa03fbb2c749a8a9
Source dataset
uspto-grants-2013_01
Patent number
US08361994B2

Reaction notes

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