Potassium Carbonate → (-)-3-acetyl-N-cyclobutylmethylmorphinan

HRID 1758505Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1758505
[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-].[K+].[K+].[CH:27]1([CH2:31]Cl)[CH2:30][CH2:29][CH2:28]1>CN(C)C=O>[C:18]([C:3]1[CH:2]=[CH:1][C:14]2[CH2:13][C@H:12]3[N:15]([CH2:31][CH:27]4[CH2:30][CH2:29][CH2:28]4)[CH2:16][CH2:17][C@@:6]4([C:5]=2[CH:4]=1)[C@H:11]3[CH2:10][CH2:9][CH2:8][CH2:7]4)(=[O:20])[CH3:19]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 13100586HCID 13100586, VerbindungHCID 23446147(Chloromethyl)cyclobutane

Produkt 1

HCID 13100589(-)-3-acetyl-N-cyclobutylmethylmorphinanAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a mixture of 1.7 g, (-)-1-(morphinan-3-yl)ethanone, 1.5 g of potassium carbonate and 40 ml dimethylformamide, was added 1.2 g of cyclobutylmethyl chloride. After the mixture had been heated at 100°-110° for 16 hours it was cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure and the residue was dissolved in 120 ml of ether. The ether solution was washed with water (2×20 ml), dried over magnesium sulfate and removal of the solvent gave 1.6 g (76%) of crude (-)-3-acetyl-N-cyclobutylmethylmorphinan. For analysis, a sample of this compound was distilled, bp 200°-210° (0.05 mm), [α]25D-80.64° (c 1.03, MeOH).

Aufarbeitung

  1. temperatureAfter the mixture had been heated at 100°-110° for 16 hours it
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. dissolutionthe residue was dissolved in 120 ml of ether
  5. washThe ether solution was washed with water (2×20 ml)
  6. dry with materialdried over magnesium sulfate and removal of the solvent

Quellen und Nachweise

ORD-Eintrag
ord-fd72a3eb433e4cdca7b00a1df87b90f1
Quelldatensatz
uspto-grants-1983_02
Patentnummer
US04374139

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