Sodium Hydroxide → HCID 53818740, compound

HRID 566544Notes

Reaction equation

HRID 566544 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 (Na2SO4). 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 (Na2SO4)
  7. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-9ed11fd316f64e08bf48e1f4383bfbbb
Source dataset
uspto-grants-2001_01
Patent number
US06174898B1

Reaction notes

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