Lithium Hydroxide → HCID 57436798, compound

HRID 2059897Notes

Reaction equation

HRID 2059897 reaction equation
[OH-].[Li+].[F:3][C:4]([F:26])([F:25])[C:5]1[CH:6]=[C:7]([S:11]([N:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH:15]2[CH2:20][C:21]([O:23]C)=[O:22])(=[O:13])=[O:12])[CH:8]=[CH:9][CH:10]=1>O.O1CCCC1>[F:26][C:4]([F:3])([F:25])[C:5]1[CH:6]=[C:7]([S:11]([N:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH:15]2[CH2:20][C:21]([OH:23])=[O:22])(=[O:13])=[O:12])[CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 58711709HCID 58711709, compound

Product 1

HCID 57436798HCID 57436798, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of lithium hydroxide (1 g, 22 mmol) in water (44 ml) was added dropwise to a solution of methyl 2-(1-(3-(trifluoromethyl)phenylsulfonyl)piperidin-2-yl)acetate (4.38 g, 12 mmol) in tetrahydrofuran (176 ml) while stirring at 0° C. The mixture was stirred for 16 h at 25° C. The solvent was removed under vacuum, the residue dissolved in water and washed with diethyl ether. The aqueous phase was carefully acidified with citric acid solution (10%) and extracted with ethyl acetate. This organic phase was washed with water and saturated sodium chloride solution, dried over sodium sulfate, filtered and concentrated to small volume under vacuum. The crude product was used in the next stage with no further purification. Yield: 90%

Workup

  1. stirringThe mixture was stirred for 16 h at 25° C
  2. customThe solvent was removed under vacuum
  3. dissolutionthe residue dissolved in water
  4. washwashed with diethyl ether
  5. extractionextracted with ethyl acetate
  6. washThis organic phase was washed with water and saturated sodium chloride solution
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated to small volume under vacuum
  10. customThe crude product was used in the next stage with no further purification

Sources & evidence

ORD record
ord-327166f8f0304d60b99def0c2983061b
Source dataset
uspto-grants-2012_10
Patent number
US08278319B2

Reaction notes

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