Sodium Hydroxide → HCID 58817653, compound

HRID 2111747Notes

Reaction equation

HRID 2111747 reaction equation
[CH3:1][O:2][C:3]([N:5]1[CH2:10][CH2:9][CH:8]([C:11]2[C:12]3[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][C:13]=3[S:14][C:15]=2[C:16]([O:18]C)=[O:17])[CH2:7][CH2:6]1)=[O:4].[OH-].[Na+]>C1COCC1.O>[CH3:1][O:2][C:3]([N:5]1[CH2:6][CH2:7][CH:8]([C:11]2[C:12]3[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:25])[F:26])=[CH:20][C:13]=3[S:14][C:15]=2[C:16]([OH:18])=[O:17])[CH2:9][CH2:10]1)=[O:4]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 58817546HCID 58817546, compound

Product 1

HCID 58817653HCID 58817653, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 4-(2-Methoxycarbonyl-6-trifluoromethyl-benzo[b]thiophen-3-yl)-piperidine-1-carboxylic acid methyl ester (1.1 g, 2.7 mmol) in THF (7.0 mL) was added 1 N NaOH (2.97 mL). The resulting mixture was stirred at room temperature overnight when the mixture was diluted with water (50 mL) and washed with ether (100 mL). The aqueous layer was acidified with the addition of 3 N HCl and the product was extracted with EtOAc (2×150 mL). The combined organic layers were washed with brine (50 mL), dried (MgSO4), filtered and evaporated yielding 960 mg (92%) of the desired product as a white solid.

Workup

  1. washwashed with ether (100 mL)
  2. additionThe aqueous layer was acidified with the addition of 3 N HCl
  3. extractionthe product was extracted with EtOAc (2×150 mL)
  4. washThe combined organic layers were washed with brine (50 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-67bc6d26b5bc469f84d9ccc889a878a6
Source dataset
uspto-grants-2009_04
Patent number
US07521445B2

Reaction notes

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