(Chloromethyl)cyclopropane → 3-Acetyl-N-(cyclpropylmethyl)morphinan

HRID 1758504Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1758504
[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+].[CH:26]1([CH2:29]Cl)[CH2:28][CH2:27]1>CN(C)C=O>[CH:26]1([CH2:29][N:15]2[CH2:16][CH2:17][C@@:6]34[C:5]5[CH:4]=[C:3]([C:18](=[O:20])[CH3:19])[CH:2]=[CH:1][C:14]=5[CH2:13][C@@H:12]2[C@@H:11]3[CH2:10][CH2:9][CH2:8][CH2:7]4)[CH2:28][CH2:27]1

Komponenten

5

Edukt 3

HCID 80013(Chloromethyl)cyclopropaneHCID 516892Sodium BicarbonateHCID 13100586HCID 13100586, Verbindung

Produkt 1

HCID 54918993-Acetyl-N-(cyclpropylmethyl)morphinanAusbeute 83,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a mixture of 0.8 g of (-)-1-(morphinan-3-yl)-ethanone, 0.6 g of sodium bicarbonate and 10 ml dimethylformamide, was added 0.3 g of cyclopropylmethyl chloride. After the mixture had been heated at reflux for 18 hours, it was cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure and the residue was dissolved in 60 ml ether. The ether solution was washed with water, dried over magnesium sulfate and removal of the solvent gave 0.8 g (83%) of crude (-)-1-[N-(cyclopropylmethyl)morphinan-3-yl]ethanone. For analysis, a sample of this compound was distilled, bp 185°-195° (0.1 mm), [α]25D-83.21° (c 1.02, MeOH).

Aufarbeitung

  1. temperatureAfter the mixture had been heated
  2. temperatureat reflux for 18 hours
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. dissolutionthe residue was dissolved in 60 ml ether
  6. washThe ether solution was washed with water
  7. dry with materialdried over magnesium sulfate and removal of the solvent

Quellen und Nachweise

ORD-Eintrag
ord-b0fc39813b9e4326a079a76273774dbd
Quelldatensatz
uspto-grants-1983_02
Patentnummer
US04374139

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