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

HRID 496216Notes

Reaction equation

HRID 496216 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, 0.216 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-95b8ad22594346e3abe77c13cd262bf4
Source dataset
uspto-grants-2005_09
Patent number
US06943188B2

Reaction notes

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