Hydroxyamine hydrochloride → (+/-)-trans-2-Ethyl-6-hydroxyimino-4a-(3-methoxyphenyl)-1,2,3,4,4a,5,6,7,8, 8a-decahydroisoquinoline

HRID 2859

Reaktionsgleichung

Reaktionsgleichung von HRID 2859
Cl.[CH2:2]([N:4]1[CH2:13][CH2:12][C@@:11]2([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=3)[C@@H:6]([CH2:7][CH2:8][C:9](=O)[CH2:10]2)[CH2:5]1)[CH3:3].Cl.[NH2:24][OH:25]>CO>[CH2:2]([N:4]1[CH2:13][CH2:12][C@@:11]2([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=3)[C@@H:6]([CH2:7][CH2:8][C:9](=[N:24][OH:25])[CH2:10]2)[CH2:5]1)[CH3:3]

Komponenten

4

Edukt 2

HCID 443297Hydroxyamine hydrochlorideHCID 86752325(+/-)-trans-2-Ethyl-4a-(3-methoxyphenyl)-6-oxo-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline hydrochloride

Produkt 1

HCID 86752324(+/-)-trans-2-Ethyl-6-hydroxyimino-4a-(3-methoxyphenyl)-1,2,3,4,4a,5,6,7,8, 8a-decahydroisoquinolineAusbeute 96,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

0.5 g (1.54 mmol) of (±)-trans-2-ethyl-4a-(3-methoxyphenyl)-6-oxo-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline hydrochloride, 0.456 g (6.56 mmol) of hydroxylamine hydrochloride and 0.64 g of KHCO3 in 10 ml of MeOH were refluxed for 45 min. The precipitate was filtered, the solvent was removed in vacuo and the residue taken up in H2O. The pH was adjusted to 8 with conc. NH4OH, the aqueous layer was extracted with CH2Cl2. The organic layer was dried, the solvent removed in vacuo, obtaining 0.45 g of the title compound which was used as such in the subsequent step.

Aufarbeitung

  1. filtrationThe precipitate was filtered
  2. customthe solvent was removed in vacuo
  3. extractionthe aqueous layer was extracted with CH2Cl2
  4. customThe organic layer was dried
  5. customthe solvent removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-4eac917dd565431a9f46b59b364b582d
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05731322

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