Hydrochloric Acid → 3-(4-Fluorophenoxy)pyrrolidine

HRID 2355167Notes

Reaction equation

HRID 2355167 reaction equation
Cl.C(OC([N:9]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[CH2:10]1)=O)(C)(C)C>O1CCOCC1.C(O)C>[F:21][C:18]1[CH:19]=[CH:20][C:15]([O:14][CH:11]2[CH2:12][CH2:13][NH:9][CH2:10]2)=[CH:16][CH:17]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 50999115Tert-butyl 3-(4-fluorophenoxy)pyrrolidine-1-carboxylate

Product 1

HCID 218981593-(4-Fluorophenoxy)pyrrolidine

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Procedure

4N hydrogen chloride in dioxane (200 ml) is added to a solution of 3-(4-fluoro-phenoxy)-pyrrolidine-1-carboxylic acid tert-butyl ester 5 (39.43 g, 140 mmol) in ethanol (200 ml) and the mixture stirred at room temperature for 18 hours. The solvent is evaporated under vacuum and the residue basified using 4N sodium hydroxide solution (200 ml). The resulting product is extracted using DCM (3×100 ml). The organic extracts are dried (using MgSO4), filtered and evaporated to give the title compound as a light brown oil.

Workup

  1. customThe solvent is evaporated under vacuum
  2. extractionThe resulting product is extracted
  3. dry with materialThe organic extracts are dried (using MgSO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-f74877a49c85405a9d30ffc0c07e2c8b
Source dataset
uspto-grants-2010_07
Patent number
US07754758B2

Reaction notes

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