N-alkyl-14-hydroxymorphinans and derivatives

Details N-alkyl-14-hydroxymorphinans and derivatives N-alkyl-14-hydroxymorphinans and derivatives

1976-12-20

1979-07-17

Daus, Donald G.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

546 44, 546 45, 546 74, C07D48908, C07D22128

Patent

active

041615972

ABSTRACT:
There is provided a novel and high yield procedure for transforming acid salts of 14-alkanoyloxymorphinans and derivatives thereof into the corresponding N-alkyl-14-hydroxymorphinans wherein the alkyl moiety on the nitrogen contains the same number of carbon atoms as that previously in the 14-alkanoyl moiety. In the process of the present invention, the acid is neutralized to the free base, the alkanoyl moiety at the 14-oxy then spontaneously shifts to the nitrogen and is subsequently reduced to the corresponding alkyl moiety. O-dealkylation at C-3, where an alkoxy group is originally present, is carried out in the usual manner. There is also provided a readily produced and readily disassociated adduct of the corresponding 14-hydroxy-N-alkanoyl morphinan-6-alkylene ketal with benzene, tetrahydrofuran, and the like.

REFERENCES:
patent: 3201403 (1965-08-01), Sawa et al.
patent: 3320262 (1967-05-01), Lewenstein et al.
patent: 3332950 (1967-07-01), Blumberg et al.
patent: 3393197 (1968-07-01), Pachter et al.
patent: 3828050 (1974-08-01), Buckett et al.
Olofson, et al., Chemical Abstracts, vol. 87, 168234z (1977).
Olofson, et al., Chemical Abstracts, vol. 87, 168235a (1977).
Olofson, et al., Chemical Abstracts, vol. 87, 168236b (1977).

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