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

HRID 910438Notes

Reaction equation

HRID 910438 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]([CH3:33])[CH2:22][C:23]2[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=2)[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]([CH3:33])[CH2:22][C:23]2[CH:28]=[CH:27][C:26]([C:29]([F:31])([F:32])[F:30])=[CH:25][CH:24]=2)[CH:18]=[CH:17][C:16]=1[Cl:19]

Participants

4

Reactant 2

HCID 870632,2,2-Trichloroethyl chloroformateHCID 67218013[(3RS,4SR)-1-Benzyl-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-methyl-(4-trifluoromethyl-benzyl)-amine

Product 1

HCID 67217816[(3RS,4SR)-4-(3,4-Dichloro-phenyl)pyrrolidin-3-yl]-methyl-(4-trifluoromethyl-benzyl)-amineYield 65.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of [(3RS,4SR)-1-benzyl-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-methyl-(4-trifluoromethyl-benzyl)-amine (160 mg, 0.32 mmol) in CH3CN (5 ml) at RT, was added 2,2,2-trichloroethyl chloroformate (0.070 ml, 0.48 mmol). The reaction mixture was stirred at RT for 3 hours, concentrated under vacuo. The residue was dissolved in AcOH (3 ml) and zinc dust (80 mg) was added portion wise over 1 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 and concentrated under vacuo. The product was purified by column chromatography (CH2Cl2/MeOH: 9/1) to afford 85 mg (65%) of the tile compound as a colorless oil. ES-MS m/e: 403.4 (M+H+).

Workup

  1. concentrationconcentrated under vacuo
  2. dissolutionThe residue was dissolved in AcOH (3 ml)
  3. additionzinc dust (80 mg) was added portion wise over 1 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
  9. customThe product was purified by column chromatography (CH2Cl2/MeOH: 9/1)

Sources & evidence

ORD record
ord-6c61ffa6177d473da6385aff1a5b97e8
Source dataset
uspto-grants-2011_09
Patent number
US08022099B2

Reaction notes

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