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

HRID 75059노트

반응식

HRID 75059 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5fe98efbc4fa4caf925e9c6cb89d86c9
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829007B2

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