Sodium Carbonate → 2-Fluoro-4-(1-methanesulfonyl-1,2,3,6-tetrahydro-pyridin-4-yl)-phenol

HRID 222588Notes

Reaction equation

HRID 222588 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2(O)[CH2:14][CH2:13][N:12]([S:15]([CH3:18])(=[O:17])=[O:16])[CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[OH:8].O1CCOCC1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC(S(O)(=O)=O)=CC=1>[F:1][C:2]1[CH:3]=[C:4]([C:9]2[CH2:14][CH2:13][N:12]([S:15]([CH3:18])(=[O:16])=[O:17])[CH2:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1[OH:8]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 668648774-(3-Fluoro-4-hydroxy-phenyl)-1-methanesulfonyl-piperidin-4-ol

Product 1

HCID 668652462-Fluoro-4-(1-methanesulfonyl-1,2,3,6-tetrahydro-pyridin-4-yl)-phenolYield 104.8%

Reagents, catalysts & solvents 1

HCID 6101p-Toluenesulfonic acidCatalyst

Conditions

Temperature
60 °C

Procedure

4-(3-Fluoro-4-hydroxy-phenyl)-1-methanesulfonyl-piperidin-4-ol (726.00 mg, 2.51 mmol) is dissolved in 1,4-dioxane (10.36 g, 10.04 mL, 117.57 mmol). p-Toluenesulfonic acid (43.65 mg, 250.93 μmol) is added and the mixture is heated at 60° C. Solid sodium carbonate is added and the reaction is concentrated. The residue is partitioned between water and ethyl acetate, the pH adjusted to 7 with 1 M hydrogen chloride and extracted with ethyl acetate. The organic layer is washed with brine, dried over magnesium sulfate, filtered, and concentrated to dryness to provide 714 mg of the title compound as a white solid. MS (m/z) 272 (M+1).

Workup

  1. concentrationthe reaction is concentrated
  2. customThe residue is partitioned between water and ethyl acetate
  3. extractionextracted with ethyl acetate
  4. washThe organic layer is washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-704f6f5952a746a08d4cb3db7e894c6d
Source dataset
uspto-grants-2012_06
Patent number
US08207344B2

Reaction notes

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