Cornforth reagent → 1-((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)-4-(pyridin-2-yl)butan-1-one

HRID 546376노트

반응식

HRID 546376 반응식
[CH:1]([C@@H:4]1[CH2:9][CH2:8][C@@H:7]([CH3:10])[CH2:6][C@H:5]1[CH:11]([OH:21])[CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1)([CH3:3])[CH3:2].[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>C(Cl)Cl>[CH:1]([C@@H:4]1[CH2:9][CH2:8][C@@H:7]([CH3:10])[CH2:6][C@H:5]1[C:11](=[O:21])[CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1)([CH3:2])[CH3:3]

참가 물질

4

반응물 2

HCID 2724130Cornforth reagentHCID 671924741-((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)-4-(pyridin-2-yl)butan-1-ol

생성물 1

HCID 671882531-((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)-4-(pyridin-2-yl)butan-1-one수율 45.6%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 1-((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)-4-(pyridin-2-yl)butan-1-ol (177 mg, 0.61 mmol) in methylene chloride (2.0 mL) were added activated 3 Å molecular sieves (0.75 g) and pyridinium dichromate (0.27 g, 3.5 mmol). The reaction was stirred overnight at room temperature then filtered through a pad of silica, which was washed with MTBE. After the organic solution was concentrated, the residue was purified by silica chromatography to give the title ketone (80 mg).

후처리

  1. filtrationthen filtered through a pad of silica, which
  2. washwas washed with MTBE
  3. concentrationAfter the organic solution was concentrated
  4. customthe residue was purified by silica chromatography

출처 및 근거

ORD 기록
ord-dd03e1437e97488e8f60b1fa3c7385af
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07935848B2

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