Potassium Hydroxide → 3-(4-(Trifluoromethyl)phenyl)pyrrolidin-3-ol

HRID 552678Notes

Reaction equation

HRID 552678 reaction equation
C(OC([N:6]1[CH2:10][CH2:9][C:8]([OH:21])([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)[CH2:7]1)=O)C.[OH-].[K+]>O1CCOCC1.C(O)CCC>[F:20][C:17]([F:18])([F:19])[C:14]1[CH:13]=[CH:12][C:11]([C:8]2([OH:21])[CH2:9][CH2:10][NH:6][CH2:7]2)=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 59030467Rac-3-hydroxy-3-(4-trifluoromethyl-phenyl)-pyrrolidine-1-carboxylic acid ethyl ester

Product 1

HCID 1208963-(4-(Trifluoromethyl)phenyl)pyrrolidin-3-olYield 57%

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 1.98 mmol rac-3-Hydroxy-3-(4-trifluoromethyl-phenyl)-pyrrolidine-1-carboxylic acid ethyl ester in 15 ml dioxane., was added 8 ml of a 2.5N solution of KOH in butanol. The solution was stirred under reflux for 2 hours. The solvent was removed in vacuo and the residue was taken in water. The aqueous phase was extracted 3 times with dichloromethane. The combined organic phases were dried over Na2SO4, evaporated and dried. The compound was suspended in hexane/ether (˜2:1), filtered and rinsed with hexane to yield the title compound (57%) as a light brown solid MS (m/e): 232.1 ([M+1], 100%).

Workup

  1. temperatureunder reflux for 2 hours
  2. customThe solvent was removed in vacuo
  3. extractionThe aqueous phase was extracted 3 times with dichloromethane
  4. dry with materialThe combined organic phases were dried over Na2SO4
  5. customevaporated
  6. customdried
  7. filtrationfiltered
  8. washrinsed with hexane

Sources & evidence

ORD record
ord-5300ece6b3ff47c4929673c6c9b01f1a
Source dataset
uspto-grants-2011_05
Patent number
US07951836B2

Reaction notes

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