Hydroxyamine hydrochloride → 2,8a-Dimethyl-4a-(3-methoxyphenyl)octahydroisoquinolin-6-one Oxime

HRID 1453970노트

반응식

HRID 1453970 반응식
[CH3:1][N:2]1[CH2:11][CH2:10][C:9]2([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=3)[C:4]([CH3:21])([CH2:5][CH2:6][CH:7](O)[CH2:8]2)[CH:3]1C.Cl.[NH2:24][OH:25]>CCO>[CH3:1][N:2]1[CH2:11][CH2:10][C:9]2([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=3)[C:4]([CH3:21])([CH2:5][CH2:6][C:7](=[N:24][OH:25])[CH2:8]2)[CH2:3]1

참가 물질

4

반응물 2

HCID 443297Hydroxyamine hydrochlorideHCID 68831190n,8a-Dimethylmethyl-4a-(3-methoxyphenyl)octahydro-6-isoquinolinol

생성물 1

HCID 729884842,8a-Dimethyl-4a-(3-methoxyphenyl)octahydroisoquinolin-6-one Oxime수율 96.5%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

N-Methyl-4aβ-(3-methoxyphenyl)octahydro-6-oxadecahydroisoquinoline 17 (1.41 g, 4.9 mmol) and hydroxylamine hydrochloride (1.70 g, 24.5 mmol) in EtOH (absolute, 100 mL) were heated to reflux for 5 h. The reaction mixture was allowed to cool to room temperature. Ethanol was removed under reduced pressure. The crude product was taken in to aqueous 2N NaOH solution (100 mL) and extracted with 3:1 CH2Cl2/THF (4×50 mL). The combined organic layers were dried (Na2SO4), filtered, and concentrated under reduced pressure yielding crude product. The crude product was purified by flash chromatography (neutral alumina, Brockmann activity II-III) eluting with 9:1 ethyl acetate/hexane to afford 1.43 g (96%) of 19 as a white solid (mixture of E/Z): LCMS (ESI): m/z 303.5 (M+H)+.

후처리

  1. temperatureto reflux for 5 h
  2. customEthanol was removed under reduced pressure
  3. extractionextracted with 3:1 CH2Cl2/THF (4×50 mL)
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customyielding crude product
  8. customThe crude product was purified by flash chromatography (neutral alumina, Brockmann activity II-III)
  9. washeluting with 9:1 ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-8311d53e8ea040ee98f115ceec353342
출처 데이터셋
uspto-grants-2009_01
특허 번호
US07476679B2

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