Methyl 2'-fluoro-2-(2-methyl-5-oxo-1-cyclopenten-1-yl)-5'-(methyloxy)-1,1'-biphenyl-4-carboxylate → Methyl 2'-fluoro-2-(2-methyl-5-oxocyclopentyl)-5'-(methyloxy)-1,1'-biphenyl-4-carboxylate

HRID 1662451

반응식

HRID 1662451 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][C:13]([C:16]([O:18][CH3:19])=[O:17])=[CH:12][C:11]=1[C:20]1[C:24](=[O:25])[CH2:23][CH2:22][C:21]=1[CH3:26]>[Pd].CCOC(C)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][C:13]([C:16]([O:18][CH3:19])=[O:17])=[CH:12][C:11]=1[CH:20]1[C:24](=[O:25])[CH2:23][CH2:22][CH:21]1[CH3:26]

참가 물질

4

반응물 1

HCID 57705608Methyl 2'-fluoro-2-(2-methyl-5-oxo-1-cyclopenten-1-yl)-5'-(methyloxy)-1,1'-biphenyl-4-carboxylate

생성물 1

HCID 57706805Methyl 2'-fluoro-2-(2-methyl-5-oxocyclopentyl)-5'-(methyloxy)-1,1'-biphenyl-4-carboxylate수율 88.4%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 8857Ethyl Acetate용매

실험 절차

A pressure tube was charged with 66.56B (0.72 g, 2.0 mmol), EtOAc (20 mL), and Pd/C (10 wt. %) (0.22 g, 0.20 mmol). The tube was purged three times with H2 at 45 psi and sealed, and the contents were stirred for 48 hours. The mixture was filtered through silica gel (EtOAc) and concentrated. The crude product was purified by silica gel flash chromatography (0-20% EtOAc/hexane) to afford 66.56C (mixture of diastereomers) (0.63 g, 87% yield) as a colorless oil.

후처리

  1. customThe tube was purged three times with H2 at 45 psi
  2. customsealed
  3. filtrationThe mixture was filtered through silica gel (EtOAc)
  4. concentrationconcentrated
  5. customThe crude product was purified by silica gel flash chromatography (0-20% EtOAc/hexane)

출처 및 근거

ORD 기록
ord-67ac87e675cf4f59b626f4fa626bf202
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08030354B2

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