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Water → {(3aR,6aS)-2-[2,4-bis(trifluoromethyl)benzyl]octahydrocyclopenta[c]pyrrol-5-yl}methanol

HRID 1620624
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HRID 1620624 반응식
Cl.[CH2:2]1[C@H:6]2[CH2:7][CH:8]([CH2:10][OH:11])[CH2:9][C@H:5]2[CH2:4][NH:3]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][C:21]=1[C:30]([F:33])([F:32])[F:31].O>CN(C=O)C>[F:31][C:30]([F:32])([F:33])[C:21]1[CH:22]=[C:23]([C:26]([F:29])([F:27])[F:28])[CH:24]=[CH:25][C:20]=1[CH2:19][N:3]1[CH2:4][C@@H:5]2[CH2:9][CH:8]([CH2:10][OH:11])[CH2:7][C@@H:6]2[CH2:2]1
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HCID 962WaterHCID 11430Potassium CarbonateHCID 5188712,4-Bis(trifluoromethyl)benzyl bromideHCID 86678792(3aR,6aS)-octahydrocyclopenta[c]pyrrol-5-ylmethanol hydrochloride

생성물 1

HCID 86678794{(3aR,6aS)-2-[2,4-bis(trifluoromethyl)benzyl]octahydrocyclopenta[c]pyrrol-5-yl}methanol수율 85.7%

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

실험 절차

To a solution of (3aR,6aS)-octahydrocyclopenta[c]pyrrol-5-ylmethanol hydrochloride (0.79 g) and potassium carbonate (1.53 g) in DMF (15 ml) was added 1-(bromomethyl)-2,4-bis(trifluoromethyl)benzene (1.5 g). The reaction mixture was stirred at room temperature for 3 hr, water was added, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (1.4 g).

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-c7a987fe52f647c0917a90755861310f
출처 데이터셋
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08772277B2

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