Short total synthesis of dihydrothebainone, dihydrocodeinone, an

Details Short total synthesis of dihydrothebainone, dihydrocodeinone, an Short total synthesis of dihydrothebainone, dihydrocodeinone, an

1982-02-19

1983-01-11

Daus, Donald G.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

546 15, 546 74, 546146, 546149, C07D48902, C07D22128, C07D21720

Patent

active

043683266

ABSTRACT:
A method of producing morphinan compounds which incorporates double advantages over the prior art, such as the utilization of .beta.,.gamma.-unsaturated ketones in place of the .alpha.,.beta.-unsaturated ketones previously used. Additionally, in the step where .beta.,.gamma.-unsaturated bromoketones (13 or 14) proceed to 1-bromo-N-formylnordihydrothebainone (morphinan) (17) there are utilized super acids, such as trifluoromethane sulfonic, trifluoroethane sulfonic and mixtures thereof, and also antimony pentafluoride and mixtures of hydrogen fluoride and antimony pentafluoride. Super acid works, whereas the prior art shows that cyclization in the presence of acids, even strong acids, such as sulfuric, phosphoric, do not work.

REFERENCES:
patent: 3438989 (1969-04-01), Shavel, Jr. et al.
patent: 4003903 (1977-01-01), Schwartz
Birch, et al., "Reduction by Metal-Ammonia Solution and Related Reagents," Advances In Organic Chemistry, vol. 8, Wiley-Interscience, 1972, pp. 1-65.
May et al., "Morphine and Its Modifications," Medicinal Chemistry, vol. 5, D. Stephens, Analgesics, 1965, pp. 123-174.
Rice, J. Org. Chem., vol. 45, No. 15, pp. 3135-3137 (07/18/80).
Herlem, Pure & Appl. Chem., vol. 49, pp. 107-113, (1977).
Gesson, et al., Chemical Abstracts, vol. 88, 152297g, (1978).
Grewe, et al., Chem. Ber., 100, 1550-1558, (1967).
Friedrichsen, Chem. Ber., 101, 1190-1194, (1968).
Maeda, et al., Chemical Abstracts, vol. 69, 52367u, (1968).
Sawa, et al., Chemical Abstracts, vol. 73, 131195x, (1970).
Hellerbach, et al., "Synthetic Analgesics," Part IIA, Morphinans, Pergamon Press, 1966, pp. 1-104.
DeGraw, et al., J. Heterocyclic Chem., vol. 11, pp. 363-367, (1974).
Beyerman, et al., Recl. Trav. Chim. Pays-Bas, 95, pp. 184-188, (1976).
Beyerman, et al., Recl. Trav. Chim. Pays-Bas, 97, pp. 127-130, (1978).
Beyerman, et al., Chemical Abstracts, 91, 74760y, (1979).
Gesson, et al., J. Chem. Soc., Chem. Comm., pp. 652-653, (1976).
Fieser, et al., Reagents for Organic Synthesis, vol. 6, John Wiley Sons, New York, 1977, pp. 617-618.

Affiliated with

Also associated with

Rating

Short total synthesis of dihydrothebainone, dihydrocodeinone, an does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Short total synthesis of dihydrothebainone, dihydrocodeinone, an, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Short total synthesis of dihydrothebainone, dihydrocodeinone, an will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-779721