2 step process for preparing biologically active tropane derivat

Details 2 step process for preparing biologically active tropane derivat 2 step process for preparing biologically active tropane derivat

1992-11-17

1994-08-30

Rotman, Alan L.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D45102

Patent

active

053429494

ABSTRACT:
Preparation of biologically active tropane derivatives of novel configurations. The compounds are prepared by decomposing vinyldiazomethanes in the presence of pyrroles to provide a bicyclic ring containing the basic tropane ring system which is then reacted with an aryl Grignard reagent in the presence of a copper (I) or (II) salt to provide 3-aryl-tropane derivatives.

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"Synthesis of (.+-.)-Ferruginine and (.+-.)-Anhydroecgonine Methyl Ester By a Tandem Cyclopropanation/Cope Rearrangement", J.Org.Chem., vol. 56, No. 19 (1991) p. 5696-5700.
Madras, et al. "Cocaine Receptors Labeled by [.sup.3 H]2.beta.-(4-Fluorophenyl Tropane", Molecular Pharmacology, 36:;518-524 (1989).
Davies, et al., "Novel Entry to the Tropane System by Reaction of Rhodium (II) Acetate Stabilized Vinylcarbenoids with Pyrroles", Tetrahedron Letters, vol. 30, No. 35, pp. 4653-4656 (1989).
Davies et al., "Chemistry of Vinylcarbenoids with a Single Electron Withdrawing Group. An Approach to Tropane Alkaloids" American Chemical Society, Dec. 5-7, 1990, pp. 181-182.

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