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tert-Butyl 4-(4-(4-(benzyloxy)-4'-(trifluoromethyl)biphenyl-3-yl)pyridin-2-yl)piperazine-1-carboxylate → Tert-butyl 4-(4-(4-hydroxy-4'-(trifluoromethyl)biphenyl-3-yl)pyridin-2-yl)piperazine-1-carboxylate

HRID 1619715
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HRID 1619715 반응식
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=2)=[CH:11][C:10]=1[C:25]1[CH:30]=[CH:29][N:28]=[C:27]([N:31]2[CH2:36][CH2:35][N:34]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:33][CH2:32]2)[CH:26]=1)C1C=CC=CC=1>C(O)C.[OH-].[OH-].[Pd+2]>[OH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[CH:17][C:18]([C:21]([F:23])([F:24])[F:22])=[CH:19][CH:20]=2)=[CH:11][C:10]=1[C:25]1[CH:30]=[CH:29][N:28]=[C:27]([N:31]2[CH2:36][CH2:35][N:34]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:33][CH2:32]2)[CH:26]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

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4

반응물 1

HCID 58042339tert-Butyl 4-(4-(4-(benzyloxy)-4'-(trifluoromethyl)biphenyl-3-yl)pyridin-2-yl)piperazine-1-carboxylate

생성물 1

HCID 136200880Tert-butyl 4-(4-(4-hydroxy-4'-(trifluoromethyl)biphenyl-3-yl)pyridin-2-yl)piperazine-1-carboxylate수율 59.1%

시약·촉매·용매 2

HCID 9942167Palladium hydroxide촉매HCID 702Ethanol용매

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온도
60 °C

실험 절차

tert-Butyl 4-(4-(4-(benzyloxy)-4′-(trifluoromethyl)biphenyl-3-yl)pyridin-2-yl)piperazine-1-carboxylate (Preparation 115, 1.30 g, 2.20 mmol) was dissolved in ethanol (20 mL) at room temperature and palladium hydroxide on activated charcoal (130 mg) was added. The reaction mixture was heated at 60° C. under a hydrogen atmosphere (50 psi) for 18 hours. The mixture was then filtered through a pad of Celite™, rinsed with ethanol and concentrated in vacuo. The residue was purified on silica gel by Biotage (5% to 60% ethyl acetate in heptane over 20 CV). Further purification by reverse phase using acetonitrile/water (5/95-95/5) with 0.1% formic acid as eluent gave the title compound (650 mg, 59%) as a white powder.

후처리

  1. filtrationThe mixture was then filtered through a pad of Celite™
  2. washrinsed with ethanol
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified on silica gel by Biotage (5% to 60% ethyl acetate in heptane over 20 CV)
  5. customFurther purification by reverse phase

출처 및 근거

ORD 기록
ord-096e3baa91c04940aa412b57f7ffdb93
출처 데이터셋
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08772293B2

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