Sodium Hydroxide → 168544-93-2

HRID 1378391Notes

Reaction equation

HRID 1378391 reaction equation
C([O:3][C:4]([C@H:6]1[C@H:10]([C:11]([F:14])([F:13])[F:12])[CH2:9][N:8]([C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[CH2:7]1)=[O:5])C.[OH-].[Na+]>C(O)C>[CH2:18]([O:17][C:15]([N:8]1[CH2:9][C@@H:10]([C:11]([F:12])([F:13])[F:14])[C@H:6]([C:4]([OH:5])=[O:3])[CH2:7]1)=[O:16])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 70207149HCID 70207149, compound

Product 1

HCID 70207030168544-93-2Yield 95.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

In 92 ml of ethanol, is dissolved 15.8 g (45.8 mmol) of trans-1-benzyloxycarbonyl-4-trifluoromethylpyrrolidine-3-carboxylic acid ethyl ester. To the above solution, is added 46 ml of 2N sodium hydroxide on cooling with ice. The mixture is stirred at 0° C. for 1 hour and then concentrated under reduced pressure. The residue is dissolved in 100 ml of water. The solution is washed with diethyl ether. The water phase is adjusted to pH 3 with citric acid. The solution is extracted twice with dichloromethane. The organic phases were put together and dried over anhydrous magnesium sulfate. The dried organic phase was concentrated under reduced pressure to give 13.84 g of the objective substance as a colorless powder (yield 95.3%).

Workup

  1. temperatureon cooling with ice
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue is dissolved in 100 ml of water
  4. washThe solution is washed with diethyl ether
  5. extractionThe solution is extracted twice with dichloromethane
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationThe dried organic phase was concentrated under reduced pressure

Sources & evidence

ORD record
ord-1666cf2ab13b4a7c8878f9347eab5387
Source dataset
uspto-grants-1997_09
Patent number
US05668147

Reaction notes

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