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

HRID 1453970ノート

反応式

HRID 1453970 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-8311d53e8ea040ee98f115ceec353342
出典データセット
uspto-grants-2009_01
特許番号
US07476679B2

反応ノート

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