Water → HCID 67170155, compound

HRID 2170844Notes

Reaction equation

HRID 2170844 reaction equation
CS(O[CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1)(=O)=O.[F:19][C:20]([F:30])([F:29])[O:21][C:22]1[CH:23]=[C:24]([SH:28])[CH:25]=[CH:26][CH:27]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[F:30][C:20]([F:19])([F:29])[O:21][C:22]1[CH:23]=[C:24]([S:28][CH:6]2[CH2:7][CH2:8][N:9]([C:12]([O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:13])[CH2:10][CH2:11]2)[CH:25]=[CH:26][CH:27]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27773573-(Trifluoromethoxy)thiophenolHCID 41848691-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidine

Product 1

HCID 67170155HCID 67170155, compoundYield 74.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of tert-butyl 4-((methylsulfonyl)oxy)piperidine-1-carboxylate (1.34 g, 4.79 mmol), 3-(trifluoromethoxy)benzenethiol (1.12 g, 5.75 mmol) and potassium carbonate (1.99 g, 14.4 mmol) in N,N-dimethylformamide (50 mL) at 90° C. for 20 hours. The mixture was poured into water (200 mL) and extracted with ethyl acetate (200 mL). The organic layer was washed with water (200 mL) and dried over sodium sulfate. After removal of the solvent, the residue was purified by column chromatography on silica gel eluting with n-hexane/ethyl acetate (20:1) to give 1.34 g (74%) of the title compound as colorless oil.

Workup

  1. extractionextracted with ethyl acetate (200 mL)
  2. washThe organic layer was washed with water (200 mL)
  3. dry with materialdried over sodium sulfate
  4. customAfter removal of the solvent
  5. customthe residue was purified by column chromatography on silica gel eluting with n-hexane/ethyl acetate (20:1)

Sources & evidence

ORD record
ord-0e765156a3454814b3acb12e41e6553c
Source dataset
uspto-grants-2015_06
Patent number
US09051296B2

Reaction notes

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