Processes for preparing morphinans and intermediates thereof

Details Processes for preparing morphinans and intermediates thereof Processes for preparing morphinans and intermediates thereof

2006-02-23

2010-11-23

Aulakh, Charanjit S (Department: 1625)

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C546S044000, C546S149000

Reexamination Certificate

active

07838677

ABSTRACT:
The present invention is directed to processes for the synthesis of morphinans. In particular, a process for cyclizing a β,γ-bicyclic ketone compound to form a nordihydrothebainone product using the Grewe cyclization reaction is improved by forming a reaction mixture comprising a β,γ-bicyclic ketone compound, a cyclizing acid and a water scavenging cyclization additive. In one embodiment, the Grewe transformation occurs in the presence of an acid anhydride as the cyclization additive. Further, the present invention is directed to processes for converting α,β-bicyclic ketone compounds (e.g., by-products of the Grewe cyclization reaction) to β,γ-bicyclic ketone compounds, wherein the β,γ-bicyclic ketone compounds may be recovered to further undergo Grewe cyclization and form the nordihydrothebainone product.

REFERENCES:
patent: 2634292 (1953-04-01), Hellerbach
patent: 2638472 (1953-05-01), Grewe
patent: 2723268 (1955-11-01), Henecka
patent: 2769810 (1956-11-01), Ochiai et al.
patent: 3914234 (1975-10-01), Mohacsi et al.
patent: 3919237 (1975-11-01), Halder
patent: 4003903 (1977-01-01), Schwartz
patent: 4058531 (1977-11-01), Monkovic et al.
patent: 4368326 (1983-01-01), Rice
patent: 4405626 (1983-09-01), Johnson
patent: 4410700 (1983-10-01), Rice
patent: 4514569 (1985-04-01), Hendrickson et al.
patent: 4521601 (1985-06-01), Rice
patent: 4556712 (1985-12-01), Rice
patent: 4613668 (1986-09-01), Rice
patent: 4727146 (1988-02-01), Rice
patent: 2003/0036550 (2003-02-01), Fedler et al.
patent: 0 155 424 (1985-09-01), None
patent: 2784986 (2000-04-01), None
patent: 1055478 (1967-01-01), None
patent: WO 2004/031204 (2004-04-01), None
Rice, “Synthetic opium alkaloids and derivatives. A short total synte\hesis of (+−)-dihydrothebainone, (+−—-dihydrocodeinone, and (+−)-nordihydrocodeinone as an approach to a practical synthesis of morphine, codeine, and congeners”, Journal of Organic chemistry, 1980, vol. 45, No. 15, pp. 3135-3137, XP002396231.
Rao et al., “11Beta-substituted 13beta-ethyl gonane derivatives exhibit reversal of antiprogestational activity” Steroids, 1998, vol. 63, No. 1, pp. 50-57, XP002396232.
Passarella et al., A Convenient Synthesis of Δ7,8-Morphinan-6-one and Its Direct Oxidation to 14-Hydroxy- Δ7,8-morphinan-6-one, Bioorganic & Medicinal Chemistry Letters 12 (2002) 1981-1983.

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