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Pentane → N-(2-Furylethyl)-4a-(m-methoxyphenyl)-1,3-diketo-cis-decahydroisoquinoline

HRID 26480
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 26480
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C@@:9]23[CH2:18][CH2:17][CH2:16][CH2:15][C@H:14]2[C:13](=[O:19])[NH:12][C:11](=[O:20])[CH2:10]3)[CH:6]=[CH:7][CH:8]=1.[H-].[Na+].CCCCC.S(O[CH2:33][CH2:34][C:35]1[O:36][CH:37]=[CH:38][CH:39]=1)(=O)(=O)C>CN(C)C=O>[O:36]1[CH:37]=[CH:38][CH:39]=[C:35]1[CH2:34][CH2:33][N:12]1[C:11](=[O:20])[CH2:10][C@@:9]2([C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=3)[C@H:14]([CH2:15][CH2:16][CH2:17][CH2:18]2)[C:13]1=[O:19]
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Komponenten

6

Edukt 4

HCID 8003PentaneHCID 24758Sodium hydrideHCID 14655779Methanesulfonic acid 2-furan-2-yl-ethyl esterHCID 867364784a-(m-Methoxyphenyl)-1,3-diketo-trans-decahydroisoquinoline

Produkt 1

HCID 86736481N-(2-Furylethyl)-4a-(m-methoxyphenyl)-1,3-diketo-cis-decahydroisoquinoline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel3×

Versuchsvorschrift

A solution of 5.0 g (18.5 mmoles) of 4a-(m-methoxyphenyl)-1,3-diketo-trans-decahydroisoquinoline in 100 ml of anhydrous dimethylformamide was added to a stirred suspension of 1.4 g (28 mmoles) of 50% sodium hydride in mineral oil (washed with pentane) in 75 ml of anhydrous dimethylformamide heated at 50° under nitrogen. The mixture was heated at 90° for 2 hours, then cooled to 35°. A solution of 7.1 g (37 mmoles) of freshly prepared 2-furylethyl mesylate (prepared according ot the procedure of Crossland and Servis, J. Org. Chem., 35, 3195 (1970)) in 10 ml of anhydrous dimethylformamide was added and the reaction mixture heated at 90° overnight. It was the cooled and poured into ice-water, and extracted with ether. Evaporation of the ether gave an oil which was purified by column chromatography (Silicar CC-7, eluting with acetone-benzene). The major fraction was identified as N-(2-furylethyl)-4a-(m-methoxyphenyl)-1,3-diketo-cis-decahydroisoquinoline

Aufarbeitung

  1. temperatureheated at 50° under nitrogen
  2. temperatureThe mixture was heated at 90° for 2 hours
  3. temperaturecooled to 35°
  4. temperaturethe reaction mixture heated at 90° overnight
  5. temperaturecooled
  6. extractionextracted with ether
  7. customEvaporation of the ether
  8. customgave an oil which
  9. customwas purified by column chromatography (Silicar CC-7, eluting with acetone-benzene)

Quellen und Nachweise

ORD-Eintrag
ord-add3d012e6f141daa579f8f76fd05db3
Quelldatensatz
uspto-grants-1979_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04150135

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