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

HRID 527100노트

반응식

HRID 527100 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-6f37c791837641a2b71ac2f1182de2ee
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09345708B2

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