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Triethylamine → [(3RS,4SR)-1-Benzyl-4-(3-chloro-phenyl)-pyrrolidin-3-yl]-(3-fluoro-4-trifluoromethyl-benzyl)-methyl-amine

HRID 910442
Notes
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Reaction equation

HRID 910442 reaction equation
[CH2:1]([N:8]1[CH2:12][CH:11]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=2)[CH:10]([NH:20][CH3:21])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[C:26]([F:34])[CH:25]=1.CCN(CC)CC>C1COCC1>[CH2:1]([N:8]1[CH2:12][CH:11]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=2)[CH:10]([N:20]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([C:30]([F:31])([F:32])[F:33])=[C:26]([F:34])[CH:25]=2)[CH3:21])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27375744-(Bromomethyl)-2-fluoro-1-(trifluoromethyl)benzeneHCID 67399567[(3RS,4SR)-1-Benzyl-4-(3-chloro-phenyl)-pyrrolidin-3-yl]-methyl-amine

Product 1

HCID 67218442[(3RS,4SR)-1-Benzyl-4-(3-chloro-phenyl)-pyrrolidin-3-yl]-(3-fluoro-4-trifluoromethyl-benzyl)-methyl-amineYield 57.4%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Conditions

Temperature
40 °C

Procedure

To a stirred solution of [(3RS,4SR)-1-benzyl-4-(3-chloro-phenyl)-pyrrolidin-3-yl]-methyl-amine (2.20 g, 7.31 mmol) in THF (70 ml) was added 4-bromomethyl-2-fluoro-1-trifluoromethyl-benzene (2.25 g, 8.75 mmol) and Et3N (1.21 ml, 8.75 mmol). The reaction mixture was stirred overnight at 40° C., concentrated under vacuo, diluted with EtOAc, washed with H2O. The organic phase was dried over Na2SO4 and the product purified by flash chromatography (SiO2, EtOAc/Heptane 1:3) to afford 2.0 g (57%) of the title compound as a colorless oil.

Workup

  1. concentrationconcentrated under vacuo
  2. additiondiluted with EtOAc
  3. washwashed with H2O
  4. dry with materialThe organic phase was dried over Na2SO4
  5. customthe product purified by flash chromatography (SiO2, EtOAc/Heptane 1:3)

Sources & evidence

ORD record
ord-bb01653f4db84a0486fc5f7ac001d8f9
Source dataset
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08022099B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes