Water → HCID 118159133, compound

HRID 713188Notes

Reaction equation

HRID 713188 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]1.[OH:22]OS([O-])=O.[K+].[OH2:28]>C1COCC1.CO>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([CH:9]1[CH2:10][CH2:11][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:13][CH2:14]1)(=[O:22])=[O:28]

Participants

6

Reactant 3

HCID 962Water2×HCID 23707502Potassium hydroxy sulfiteHCID 118159157HCID 118159157, compound

Product 1

HCID 118159133HCID 118159133, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of tert-butyl 4-((2-fluorophenyl)thio)piperidine-1-carboxylate (1.98 g, 6.36 mmol) in THF (54.5 mL) and MeOH (18.2 mL) at 0° C. was treated with a cold solution of Oxone® (9.77 g, 15.9 mmol) in water (54.5 mL). The reaction mixture was stirred for 5 h, gradually warming to room temperature. The reaction mixture was poured into water and extracted twice with EtOAc. The combined organics were washed with water and then saturated aqueous NaCl, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by flash silica gel chromatography using a gradient of 10% to 50% EtOAc with 0.1% triethylamine in heptanes gave tert-butyl 4-((2-fluorophenyl)sulfonyl)piperidine-1-carboxylate as a pale yellow oil (1.31 g, 60%).

Workup

  1. extractionextracted twice with EtOAc
  2. washThe combined organics were washed with water
  3. dry with materialsaturated aqueous NaCl, dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash silica gel chromatography

Sources & evidence

ORD record
ord-d1b8529561e94ecea38ea2018e970794
Source dataset
uspto-grants-2015_11
Patent number
US09181249B2

Reaction notes

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