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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
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HRID 910442 반응식
[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
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HCID 8471TriethylamineHCID 27375744-(Bromomethyl)-2-fluoro-1-(trifluoromethyl)benzeneHCID 67399567[(3RS,4SR)-1-Benzyl-4-(3-chloro-phenyl)-pyrrolidin-3-yl]-methyl-amine

생성물 1

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

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

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온도
40 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-bb01653f4db84a0486fc5f7ac001d8f9
출처 데이터셋
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08022099B2

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