Methylenetriphenylphosphorane → 17-Cyclopropylmethyl-3-hydroxy-6-methylene-morphinan

HRID 128214

Reaktionsgleichung

Reaktionsgleichung von HRID 128214
[CH:1]1([CH2:4][N:5]2[CH2:22][CH2:21][C@@:12]34[C:13]5[CH:14]=[C:15]([OH:20])[CH:16]=[CH:17][C:18]=5[CH2:19][C@@H:6]2[C@@H:7]3[CH2:8][CH2:9][C:10](=O)[CH2:11]4)[CH2:3][CH2:2]1.[CH2:24]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>CS(C)=O>[CH:1]1([CH2:4][N:5]2[CH2:22][CH2:21][C@@:12]34[C:13]5[CH:14]=[C:15]([OH:20])[CH:16]=[CH:17][C:18]=5[CH2:19][C@@H:6]2[C@@H:7]3[CH2:8][CH2:9][C:10](=[CH2:24])[CH2:11]4)[CH2:2][CH2:3]1

Komponenten

4

Edukt 2

HCID 137960MethylenetriphenylphosphoraneHCID 660225717-Cyclopropylmethyl-3-hydroxy-morphinan-6-one

Produkt 1

HCID 5441248517-Cyclopropylmethyl-3-hydroxy-6-methylene-morphinan

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

Reaction of 17-cyclopropylmethyl-3-hydroxy-morphinan-6-one (1.58 g, 5 mmole) with methylenetriphenylphosphorane (20 mmole) in dimethyl sulfoxide gave a crude residue which was chromatographed using 10:1 chloroform-methanol containing 1% concentrated ammonium hydroxide. Pure fractions were pooled to give 909 mg (58%) of TR-5609 which crystallized from ethanol to give 532 mg of analytically pure TR-5609, mp 220°-223°.

Quellen und Nachweise

ORD-Eintrag
ord-d7ffcb5aa64b450d96fe70fcc9e98e58
Quelldatensatz
uspto-grants-1981_03
Patentnummer
US04259329

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