(-)-3-Acetylmorphinan-17-carboxylic acid (trichloroethyl)ester → HCID 13100586, Verbindung

HRID 1758503Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1758503
ClC(Cl)(Cl)COC([N:7]1[CH2:26][CH2:25][C@@:14]23[C:15]4[CH:16]=[C:17]([C:22](=[O:24])[CH3:23])[CH:18]=[CH:19][C:20]=4[CH2:21][C@@H:8]1[C@@H:9]2[CH2:10][CH2:11][CH2:12][CH2:13]3)=O>C(O)(=O)C.[Zn]>[CH:19]1[C:20]2[CH2:21][C@H:8]3[NH:7][CH2:26][CH2:25][C@:14]4([C@H:9]3[CH2:10][CH2:11][CH2:12][CH2:13]4)[C:15]=2[CH:16]=[C:17]([C:22](=[O:24])[CH3:23])[CH:18]=1

Komponenten

4

Edukt 1

HCID 13100607(-)-3-Acetylmorphinan-17-carboxylic acid (trichloroethyl)ester

Produkt 1

HCID 13100586HCID 13100586, VerbindungAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysatorHCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

To a solution of 2.4 g of (-)-3-acetylmorphinan-17-carboxylic acid (trichloroethyl)ester in 40 ml of 90% acetic acid was added portionwise, 2.5 g of zinc-dust. The mixture was stirred at room temperature for 16 hours and filtered. The filtrate was concentrated in vacuo and the residue was partitioned between 40 ml ether and dilute ammonium hydroxide. The ether solution was extracted with 60 ml of 4 N hydrochloric acid. The acidic solution was basified with concentrated ammonium hydroxide and extracted with ether (2×30 ml). The ether solution was dried over magnesium sulfate and removal of the solvent gave 1.0 g (71%) of crude (-)-1-(morphinan-3-yl)ethanone. For analysis, a sample of this compound was distilled, bp 165°-175° (0.1 mm), [α]25D-24.77° (c 1.06, MeOH).

Aufarbeitung

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated in vacuo
  3. customthe residue was partitioned between 40 ml ether and dilute ammonium hydroxide
  4. extractionThe ether solution was extracted with 60 ml of 4 N hydrochloric acid
  5. extractionextracted with ether (2×30 ml)
  6. dry with materialThe ether solution was dried over magnesium sulfate and removal of the solvent

Quellen und Nachweise

ORD-Eintrag
ord-5a760000605a48baab7f1b08cf0696aa
Quelldatensatz
uspto-grants-1983_02
Patentnummer
US04374139

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