4-Toluenesulfonyl chloride → HCID 86707287, compound

HRID 576084Notes

Reaction equation

HRID 576084 reaction equation
Cl.CN(C)C.C(N(CC)CC)C.[F:13][C@H:14]1[C@@H:19]([CH2:20][CH2:21][OH:22])[CH2:18][CH2:17][O:16][CH2:15]1.[C:23]1([CH3:33])[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=1>C1(C)C=CC=CC=1.O>[CH3:33][C:23]1[CH:28]=[CH:27][C:26]([S:29]([O:22][CH2:21][CH2:20][C@H:19]2[CH2:18][CH2:17][O:16][CH2:15][C@H:14]2[F:13])(=[O:31])=[O:30])=[CH:25][CH:24]=1

Participants

7

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 10313079Trimethylamine HydrochlorideHCID 86707288HCID 86707288, compound

Product 1

HCID 86707287HCID 86707287, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

Trimethylamine hydrochloride (128 mg, 1.34 mmol) and triethylamine (0.39 mL, 2.81 mmol) were added to a solution of (±)-cis-2-(3-fluorotetrahydro-2 H-pyran-4-yl)ethanol obtained (198 mg, 1.34 mmol) in toluene (5 mL). Subsequently, p-toluenesulfonyl chloride (382 mg, 2.00 mmol) was added thereto while cooling in ice, and the mixture was stirred for 1 hr. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. After the desiccant was filtered off, the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane only→hexane:ethyl acetate=1:1) to afford the title compound (354 mg) as a colorless oil.

Workup

  1. temperaturewhile cooling in ice
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationAfter the desiccant was filtered off
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (hexane only→hexane

Sources & evidence

ORD record
ord-c6debdfb8a974dfaafaae8435c1cfb0a
Source dataset
uspto-grants-2015_05
Patent number
US09035059B2

Reaction notes

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