Sodium Hydroxide → HCID 57436798, compound

HRID 45987Notes

Reaction equation

HRID 45987 reaction equation
[F:1][C:2]([F:25])([F:24])[C:3]1[CH:4]=[C:5]([S:9]([N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]2[CH2:18][C:19]([O:21]CC)=[O:20])(=[O:11])=[O:10])[CH:6]=[CH:7][CH:8]=1.[OH-].[Na+]>CO.O1CCOCC1>[F:25][C:2]([F:1])([F:24])[C:3]1[CH:4]=[C:5]([S:9]([N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]2[CH2:18][C:19]([OH:21])=[O:20])(=[O:11])=[O:10])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 57819731HCID 57819731, compound

Product 1

HCID 57436798HCID 57436798, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

The ethyl 2-(1-(3-(trifluoromethyl)phenylsulfonyl)piperidin-2-yl)acetate (10.45 g, 27.5 mmol) was dissolved in a mixture of methanol (150 ml), dioxane (40 ml) and aqueous NaOH solution (4 M, 41.3 ml, 165.2 mmol, 6 eq.) and the solution was stirred overnight When the reaction had ended (TLC control, MC/methanol 95:5), the solution was concentrated. The crude product was taken up in ethyl acetate (600 ml) and the mixture was . . . with KHSO4 solution (0.5 M, 600 ml). The aqueous phase was extracted once more with ethyl acetate (100 ml) and the combined organic phases were washed with sat. NaCl solution (500 ml), dried over Na2SO4 and concentrated. Yield: 9.4 g, 97%.

Workup

  1. concentrationthe solution was concentrated
  2. extractionThe aqueous phase was extracted once more with ethyl acetate (100 ml)
  3. washthe combined organic phases were washed with sat. NaCl solution (500 ml)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e68a6fb3c19b4a778a2232070437c467
Source dataset
uspto-grants-2013_09
Patent number
US08541573B2

Reaction notes

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