2-Butene, 1-bromo-3-methyl- → (-)-1-[17-(3-Methyl-2-butenyl)morphinan-3-yl]ethanone

HRID 1758508Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1758508
[CH:1]1[C:14]2[CH2:13][C@H:12]3[NH:15][CH2:16][CH2:17][C@:6]4([C@H:11]3[CH2:10][CH2:9][CH2:8][CH2:7]4)[C:5]=2[CH:4]=[C:3]([C:18](=[O:20])[CH3:19])[CH:2]=1.C(=O)(O)[O-].[Na+].[CH3:26][C:27]([CH3:31])=[CH:28][CH2:29]Br>CN(C)C=O>[CH3:26][C:27]([CH3:31])=[CH:28][CH2:29][N:15]1[CH2:16][CH2:17][C@@:6]23[C:5]4[CH:4]=[C:3]([C:18](=[O:20])[CH3:19])[CH:2]=[CH:1][C:14]=4[CH2:13][C@@H:12]1[C@@H:11]2[CH2:10][CH2:9][CH2:8][CH2:7]3

Komponenten

5

Edukt 3

HCID 700922-Butene, 1-bromo-3-methyl-HCID 516892Sodium BicarbonateHCID 13100586HCID 13100586, Verbindung

Produkt 1

HCID 13100605(-)-1-[17-(3-Methyl-2-butenyl)morphinan-3-yl]ethanoneAusbeute 93,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a mixture of 1.8 g of (-)-1-(morphinan-3-yl)ethanone, 0.6 g of sodium bicarbonate and 25 ml of dimethylformamide, was added 1.0 g of dimethylallyl bromide. After the mixture had been heated at 50° for 16 hours, it was cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure and the residue was partitioned between 50 ml of methylene chloride and 30 ml of water. The methylene chloride solution was washed with water and dried over magnesium sulfate. Removal of the solvent gave 2.1 g (93%) of crude (-)-1-[17-(3-methyl-2-butenyl)morphinan-3-yl]ethanone. For analysis, a sample of this compound was distilled, bp 185°-195° (0.05 mm), [α]25D-76.53° (c 0.98, MeOH).

Aufarbeitung

  1. temperatureAfter the mixture had been heated at 50° for 16 hours
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe residue was partitioned between 50 ml of methylene chloride and 30 ml of water
  5. washThe methylene chloride solution was washed with water
  6. dry with materialdried over magnesium sulfate
  7. customRemoval of the solvent

Quellen und Nachweise

ORD-Eintrag
ord-7dd742878f7a437b8fa4a841a19ef86a
Quelldatensatz
uspto-grants-1983_02
Patentnummer
US04374139

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