Water → Tert-butyl 3-(4-fluorophenoxy)pyrrolidine-1-carboxylate

HRID 2355166Notes

Reaction equation

HRID 2355166 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[C:11]([O:15][C:16]([N:18]1[CH2:22][CH2:21][CH:20](OS(C)(=O)=O)[CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12].O>CN(C=O)C>[C:11]([O:15][C:16]([N:18]1[CH2:22][CH2:21][CH:20]([O:10][C:7]2[CH:8]=[CH:9][C:4]([F:3])=[CH:5][CH:6]=2)[CH2:19]1)=[O:17])([CH3:14])([CH3:12])[CH3:13]

Participants

6

Reactant 4

HCID 962WaterHCID 97324-FluorophenolHCID 24758Sodium hydrideHCID 4139999Tert-butyl 3-(methanesulfonyloxy)pyrrolidine-1-carboxylate

Product 1

HCID 50999115Tert-butyl 3-(4-fluorophenoxy)pyrrolidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (554 mg, 13.84 mmol) is added to a solution of 4-fluorophenol (1.60 g, 14.20 mmol) in DMF (20 ml) and the mixture is stirred at room temperature for 2 minutes. 3-Methanesulphonyloxy-pyrrolidine-1-carboxylic acid tert-butyl ester is added and the mixture heated at 60° C. for 18 hours. Water (50 ml) is then added and the resulting product is extracted using diethyl ether (3×30 ml). The organic extracts are dried (using MgSO4), filtered and evaporated to give a white solid, which is purified using column chromatography over silica gel (ethyl acetate/isohexane 1:9 v/v) to give the title compound.

Workup

  1. temperaturethe mixture heated at 60° C. for 18 hours
  2. extractionthe resulting product is extracted
  3. dry with materialThe organic extracts are dried (using MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customto give a white solid, which
  7. customis purified

Sources & evidence

ORD record
ord-838d9f217a5c4999840f39bdda842bb6
Source dataset
uspto-grants-2010_07
Patent number
US07754758B2

Reaction notes

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