Selective chlorination of steroids and other substrates directed

Details Selective chlorination of steroids and other substrates directed Selective chlorination of steroids and other substrates directed

1987-05-28

1990-04-24

Lipovsky, Joseph A.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

552595, 552544, 552574, 552576, 552566, C07J 4300, C07J 100

Patent

active

049202162

ABSTRACT:
This invention concerns a method of substituting a chlorine atom for a predetermined hydrogen atom located within an organic compound which comprises contacting the organic compound containing the predetermined hydrogen atom with an esterifying agent comprising a pyridine ring or a substituted or fused ring derivative of a pyridine ring so as to produce an ester and treating the ester with a chlorinating agent so as to substitute the chlorine atom for the predetermined hydrogen atom. The ester comprises the pyridine ring or the substituted or fused ring derivative of the pyridine ring so positioned within the ester with respect to the predetermined hydrogen atom that a chlorine atom attached to the nitrogen atom of the pyridine ring or substituted or fused ring derivative of the pyridine ring reacts with the predetermined hydrogen atom.
Another aspect of the invention is a method for converting a predetermined single bond between a carbon atom and another atom in an organic compound into a double bond between the carbon atom and the other atom which comprises substituting a chlorine atom for a predetermined hydrogen atom bound to the carbon atom or the other atom of the organic compound according to the method of this invention so as to produce a chlorine-containing compound and then treating the chlorine-containing compound so as to eliminate the chlorine atom from the compound and form the double bond.

REFERENCES:
Journal of the American Chemical Society, vol. 109 No. 12; pp. 3799-3801; Jun. 10, 1987; Breslow et al.

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