Pyridine → (1R,5S)-6,6-dimethylbicyclo[3.1.1]heptan-2-one O-methyl oxime

HRID 75059ノート

反応式

HRID 75059 の反応式
[CH3:1][C:2]1([CH3:10])[C@@H:7]2[CH2:8][C@H:3]1[CH2:4][CH2:5][C:6]2=O.Cl.[CH3:12][O:13][NH2:14].N1C=CC=CC=1>C(O)C>[CH3:12][O:13][N:14]=[C:6]1[CH2:5][CH2:4][C@H:3]2[CH2:8][C@@H:7]1[C:2]2([CH3:10])[CH3:1]

参加物

5

反応物 3

HCID 1049PyridineHCID 157139Bicyclo(3.1.1)heptan-2-one, 6,6-dimethyl-, (1S,5R)-HCID 521874O-Methylhydroxylamine hydrochloride

生成物 1

HCID 86667458(1R,5S)-6,6-dimethylbicyclo[3.1.1]heptan-2-one O-methyl oxime収率 89.9%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a solution of (1S,5R)-6,6-dimethylnorpinan-2-one (3.09 g, 22.35 mmol) in ethanol (70 mL) was added O-methylhydroxylamine hydrochloride (2.05 g, 24.59 mmol) and pyridine (1.29 mL, 15.92 mmol). Heated reaction mixture to 80° C. for 4 hours. Removed solvent under reduced pressure. Diluted residue with 1N HCl and extracted twice with ether. The combined organic phases were washed with aqueous saturated NaHCO3, dried (MgSO4), filtered, concentrated in vacuo to afford 3.36 g of a colorless oil (mixture of oxime isomers) that was used without further purification.

後処理

  1. temperatureHeated
  2. customreaction mixture to 80° C. for 4 hours
  3. extractionDiluted residue with 1N HCl and extracted twice with ether
  4. washThe combined organic phases were washed with aqueous saturated NaHCO3
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-5fe98efbc4fa4caf925e9c6cb89d86c9
出典データセット
uspto-grants-2014_09
特許番号
US08829007B2

反応ノート

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