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

HRID 546376ノート

反応式

HRID 546376 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-dd03e1437e97488e8f60b1fa3c7385af
出典データセット
uspto-grants-2011_05
特許番号
US07935848B2

反応ノート

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