Water → HCID 18538977, compound

HRID 856075Notes

Reaction equation

HRID 856075 reaction equation
[F:1][C:2]([F:12])([F:11])[O:3][C:4]1[CH:9]=[CH:8][C:7]([SH:10])=[CH:6][CH:5]=1.[H-].[Na+].C1(C)C=CC(S(O[CH:25]2[CH2:30][CH2:29][N:28]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:27][CH2:26]2)(=O)=O)=CC=1.O>C1COCC1>[F:12][C:2]([F:1])([F:11])[O:3][C:4]1[CH:5]=[CH:6][C:7]([S:10][CH:25]2[CH2:30][CH2:29][N:28]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:27][CH2:26]2)=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 27773604-(Trifluoromethoxy)thiophenolHCID 157347131-(tert-Butoxycarbonyl)-4-(p-toluenesulfonyloxy)piperidine

Product 1

HCID 18538977HCID 18538977, compoundYield 80.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-(Trifluoromethoxy)thiophenol (2.0 g, 10.3 mmol) was dissolved in THF (30 ml), and this solution was cooled in an ice-bath. To which sodium hydride (453 mg, 11.3 mmol) was added, and the mixture was stirred for 30 minutes. To which tert-butyl 4-(toluene-4-sulfonyloxy)piperidine-1-carboxylate (3.66 g, 10.3 mmol) prepared in Reference Example 137 was added, and the resulting mixture was stirred at room temperature for 30 minutes, and then heated under reflux for 1 hour. Water was added to the reaction mixture, and the mixture was extracted with methylene chloride. The extract was dried over magnesium sulfate, and then filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane/ethyl chloride=20/1) to afford tert-butyl 4-(4-trifluoromethoxyphenylsulfanyl)piperidine-1-carboxylate (3.12 g, yield 80%) as a colorless oil.

Workup

  1. temperaturethis solution was cooled in an ice-bath
  2. additionwas added
  3. stirringthe resulting mixture was stirred at room temperature for 30 minutes
  4. temperatureheated
  5. temperatureunder reflux for 1 hour
  6. extractionthe mixture was extracted with methylene chloride
  7. dry with materialThe extract was dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationthe filtrate was concentrated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (n-hexane/ethyl chloride=20/1)

Sources & evidence

ORD record
ord-d882bee4e2884993aaf7ea88ca6fee5e
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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