Sodium Hydroxide → HCID 53818740, compound

HRID 1614814Notes

Reaction equation

HRID 1614814 reaction equation
C([O:3][C:4]([C@@H:6]1[CH2:11][CH2:10][CH2:9][N:8]([CH2:12][CH2:13][O:14][CH2:15][CH:16]=[C:17]([C:28]2[CH:33]=[CH:32][C:31]([C:34]([F:37])([F:36])[F:35])=[CH:30][CH:29]=2)[C:18]2[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=2)[CH2:7]1)=[O:5])C.[OH-].[Na+]>C(O)C>[F:37][C:34]([F:35])([F:36])[C:31]1[CH:32]=[CH:33][C:28]([C:17]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=2)=[CH:16][CH2:15][O:14][CH2:13][CH2:12][N:8]2[CH2:9][CH2:10][CH2:11][C@@H:6]([C:4]([OH:5])=[O:3])[CH2:7]2)=[CH:29][CH:30]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 53789286HCID 53789286, compound

Product 1

HCID 53818740HCID 53818740, compoundYield 105%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(R)-N-(2-(3,3-bis(4-(trifluoromethyl)phenyl)-2-propen-1-yloxy)ethyl)-3-piperidinecarboxylic acid ethyl ester (2.0 g, 3.8 mmol) was dissolved in ethanol (30 ml) and a 1 M sodium hydroxide solution (17 ml) was added. The reaction mixture was stirred at room temperature for 3 h. The solvent was evaporated in vacuo and dichloromethane (100 ml) was added. A concentrated hydrochloric acid solution was added (1.9 ml) and the phases were separated. Ethyl acetate was added to the organic phase which was then dried over sodium sulphate. The solvent was evaporated in vacuo to give 2.0 g (99%) of the title compound as a solid.

Workup

  1. customThe solvent was evaporated in vacuo and dichloromethane (100 ml)
  2. additionwas added
  3. additionA concentrated hydrochloric acid solution was added (1.9 ml)
  4. customthe phases were separated
  5. additionEthyl acetate was added to the organic phase which
  6. dry with materialwas then dried over sodium sulphate
  7. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-725667e2415f474190fedef378386a3e
Source dataset
uspto-grants-1993_03
Patent number
US05198451

Reaction notes

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