Process for the preparation of oxabispidines

Organic compounds -- part of the class 532-570 series – Organic compounds – Chalcogen in the nitrogen containing substituent

Reexamination Certificate

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C560S009000

Reexamination Certificate

active

10474593

ABSTRACT:
There is provided a process for the preparation of a compound of formula (I): which process comprises reaction of a compound of formula (II): with either a compound of formula (III): or acrylamide, followed, in the latter case, by reaction of the resulting intermediate of formula (IV): with an alcohol of formula R2—OH and an agent that promotes, or agents that in combination promote, rearrangement and oxidation of the compound of formula IV to an intermediate isocyanate, which may then react with the alcohol of formula R2—OH, and wherein R1, R2and R16have meanings given in the description

REFERENCES:
patent: 3196154 (1965-07-01), Steck
patent: WO-91/07405 (1991-05-01), None
patent: WO-01/28992 (2001-04-01), None
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Paudler et al., “3,7-Disubstituted Octahydro-1,5-diazocines. Their Conversion into Tetrahydro-1,5-diazocines and into Ring-Contracted Products,” J. Org. Chem. 32:2425-2430 (1967).
Rubtsov et al., “Synthesis and Pharmacological Investigation of Derivatives of 9-Methyl-3,9-diazabicyclo-(3,3,1)-nonane,” Journal of Medicinal and Pharmaceutical Chemistry, 3(3):441-459 (1961).
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