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

HRID 546376Notes

Reaction equation

HRID 546376 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-dd03e1437e97488e8f60b1fa3c7385af
Source dataset
uspto-grants-2011_05
Patent number
US07935848B2

Reaction notes

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