Water → HCID 67167745, compound

HRID 2170842Notes

Reaction equation

HRID 2170842 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][CH:21]=1)[O:5][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.C(=O)([O-])[O-].[Cs+].[Cs+].FC(F)(F)S(O[CH2:34][C:35]([F:38])([F:37])[F:36])(=O)=O.O>CN(C)C=O>[F:36][C:35]([F:38])([F:37])[CH2:34][O:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][CH:21]=1)[O:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:16])[CH3:17])=[O:13])[CH2:8][CH2:7]1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 60047515HCID 60047515, compound

Product 1

HCID 67167745HCID 67167745, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of tert-butyl 4-(3-hydroxyphenoxy)piperidine-1-carboxylate (2.00 g, 6.82 mmol) and cesium carbonate (4.44 g, 13.6 mmol) in N,N-dimethylformamide (25 mL) was added 2,2,2-trifluoroethyl trifluoromethane-sulfonate (1.74 g, 7.50 mmol) at room temperature. After stirring at room temperature for 2 hours, the mixture was poured into water (100 mL) and extracted with ethyl acetate (100 mL). The organic layer was washed with water (100 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 (4:1) to give 2.42 g (95%) of the title compound as colorless oil.

Workup

  1. extractionextracted with ethyl acetate (100 mL)
  2. washThe organic layer was washed with water (100 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 (4:1)

Sources & evidence

ORD record
ord-b88dff1e4dda44ac8720f1db256a19e4
Source dataset
uspto-grants-2015_06
Patent number
US09051296B2

Reaction notes

Loading…