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

HRID 965918Notes

Reaction equation

HRID 965918 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-6f091828a83c46788ff7ede460f8c37a
Source dataset
uspto-grants-2005_10
Patent number
US06951874B2

Reaction notes

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