2,2,2-Trichloroethyl chloroformate → [(3RS,4SR)-4-(3,4-Dichloro-phenyl)-pyrrolidin-3-yl]-(3-fluoro-4-trifluoromethyl-benzyl)-methyl-amine

HRID 910431Notes

Reaction equation

HRID 910431 reaction equation
C([N:8]1[CH2:12][CH:11]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([Cl:20])[CH:14]=2)[CH:10]([N:21]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[C:26]([F:34])[CH:25]=2)[CH3:22])[CH2:9]1)C1C=CC=CC=1.ClC(OCC(Cl)(Cl)Cl)=O>CC#N>[Cl:20][C:15]1[CH:14]=[C:13]([CH:11]2[CH2:12][NH:8][CH2:9][CH:10]2[N:21]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([C:30]([F:32])([F:33])[F:31])=[C:26]([F:34])[CH:25]=2)[CH3:22])[CH:18]=[CH:17][C:16]=1[Cl:19]

Participants

4

Reactant 2

HCID 870632,2,2-Trichloroethyl chloroformateHCID 86641315[(3RS,4SR)-1-Benzyl-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-(3-fluoro-4-trifluoromethyl-benzyl)-methyl-amine

Product 1

HCID 75231672[(3RS,4SR)-4-(3,4-Dichloro-phenyl)-pyrrolidin-3-yl]-(3-fluoro-4-trifluoromethyl-benzyl)-methyl-amineYield 53%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of [(3RS,4SR)-1-benzyl-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-(3-fluoro-4trifluoromethyl-benzyl)-methyl-amine (3.30 g, 6.45 mmol) in CH3CN (45 ml) at RT, was added 2,2,2-trichloroethyl chloroformate (1.30 ml, 9.67 mmol). The reaction mixture was stirred at RT for 3 hours, concentrated under vacuo. The residue was dissolved in AcOH (10 ml) and zinc dust (1.0 g) was added portion wise over 3 hours. The solvent was evaporated, the residue diluted in EtOAc and the organic phase was washed with an aqueous solution of NaHCO3. The organic phase was dried over Na2SO4, concentrated under vacuo to afford 1.43 g (53%) of the tile compound as a colorless oil. ES-MS m/e: 421.0 (M+H+).

Workup

  1. concentrationconcentrated under vacuo
  2. dissolutionThe residue was dissolved in AcOH (10 ml)
  3. additionzinc dust (1.0 g) was added portion wise over 3 hours
  4. customThe solvent was evaporated
  5. additionthe residue diluted in EtOAc
  6. washthe organic phase was washed with an aqueous solution of NaHCO3
  7. dry with materialThe organic phase was dried over Na2SO4
  8. concentrationconcentrated under vacuo

Sources & evidence

ORD record
ord-3a487388ce294e73b1c9aa01b2014517
Source dataset
uspto-grants-2011_09
Patent number
US08022099B2

Reaction notes

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