Nitrogen → (5alpha,6beta)-4,5-Epoxy-3-methoxy-17-methylmorphinan-6-ol

HRID 372155

Reaktionsgleichung

Reaktionsgleichung von HRID 372155
[CH3:1][N:2]1[CH2:21][CH2:20][C@:9]23[C:10]4[C:11]5[O:19][C@H:8]2[C:7](=[O:22])[CH2:6][CH2:5][C@H:4]3[C@H:3]1[CH2:16][C:15]=4[CH:14]=[CH:13][C:12]=5[O:17][CH3:18].[OH-].[Na+].C(S(O)=O)(N)=N.N#N>C(O)C.CO>[CH3:1][N:2]1[C@@H:3]2[CH2:16][C:15]3[CH:14]=[CH:13][C:12]([O:17][CH3:18])=[C:11]4[O:19][C@H:8]5[C@H:7]([OH:22])[CH2:6][CH2:5][C@@H:4]2[C@:9]5([C:10]=34)[CH2:20][CH2:21]1

Komponenten

7

Edukt 4

HCID 947NitrogenHCID 14798Sodium HydroxideHCID 61274Thiourea dioxideHCID 5284569Hydrocodone

Produkt 1

HCID 5492898(5alpha,6beta)-4,5-Epoxy-3-methoxy-17-methylmorphinan-6-ol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 887MethanolLösungsmittel

Versuchsvorschrift

75 mg. (0.25 mmol.) of 17-methyl-4,5α-epoxy-3-methoxymorphinan-6-one is dissolved in 20 ml. of methanol. The resulting solution is treated with 10 ml. of aqueous sodium hydroxide (150 mg.) containing 95 mg. (0.88 mmol.) formamidinesulfinic acid. The resulting mixture is magnetically stirred for one hour at 80° C. under a current of N2. The reaction mixture is thereafter stripped of ethanol and extracted with chloroform. Upon evaporation of chloroform, a residue of dihydroisocodeine is obtained. The NMR spectrum (CDCl3) of the dihydroisocodeine product is identical with that of the published reference spectrum (see S. Okuda et al., Chem. Pharm. Bull., 12, 104 (1964). The dihydroisocodeine free base is converted to its hydrochloride which has no melting point below 300° C.

Aufarbeitung

  1. additionThe resulting solution is treated with 10 ml
  2. extractionextracted with chloroform
  3. customUpon evaporation of chloroform

Quellen und Nachweise

ORD-Eintrag
ord-f8ee8f43aef24b3bbfeb5ca0c5e8530d
Quelldatensatz
uspto-grants-1978_05
Patentnummer
US04089855

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