3-(4-Chlorophenoxy)pyrrolidine → 1-[3-(4-Chlorophenoxy)-1-pyrrolidinyl]-3-(3,5-difluoro-2-nitrophenoxy)-2-propanol

HRID 584637Notes

Reaction equation

HRID 584637 reaction equation
[Cl:1][C:2]1[CH:13]=[CH:12][C:5]([O:6][CH:7]2[CH2:11][CH2:10][NH:9][CH2:8]2)=[CH:4][CH:3]=1.[F:14][C:15]1[C:16]([N+:27]([O-:29])=[O:28])=[C:17]([CH:23]=[C:24]([F:26])[CH:25]=1)[O:18][CH2:19][CH:20]1[CH2:22][O:21]1>C(O)C>[Cl:1][C:2]1[CH:13]=[CH:12][C:5]([O:6][CH:7]2[CH2:11][CH2:10][N:9]([CH2:22][CH:20]([OH:21])[CH2:19][O:18][C:17]3[CH:23]=[C:24]([F:26])[CH:25]=[C:15]([F:14])[C:16]=3[N+:27]([O-:29])=[O:28])[CH2:8]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 129995703-(4-Chlorophenoxy)pyrrolidineHCID 223137492-[(3,5-Difluoro-2-nitrophenoxy)methyl]oxirane

Product 1

HCID 223136121-[3-(4-Chlorophenoxy)-1-pyrrolidinyl]-3-(3,5-difluoro-2-nitrophenoxy)-2-propanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-(4-chlorophenoxy)pyrrolidine and 2-[(3,5-difluoro-2-nitrophenoxy)methyl]oxirane (50 mg, 0.21 mmol) in ethanol was refluxed for 3 hrs. The solvent was distilled off under reduced pressure and the resulting residue purified by silica gel column chromatography (dichloromethane/methanol 20:1) to give 45 mg (0.105 mmol) of the title compound as solid.

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. customthe resulting residue purified by silica gel column chromatography (dichloromethane/methanol 20:1)

Sources & evidence

ORD record
ord-c1d13fca55c043e699122f507fb739c8
Source dataset
uspto-grants-2005_08
Patent number
US06927222B2

Reaction notes

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