C-15 phosphonate reagent compositions and methods of synthesizing the same
AssigneeLoyola University of Chicage
InventorJames H. Babler
Life of this patent
Estimating the term…
Abstract
Allenic phosphonate reagent compositions are described which have the formula: ##STR1## wherein R and R'=C.sub.1 -C.sub.4 alkyl groups, or R, R'=(CH.sub.2).sub.n (n=2 or 3) or CH.sub.2 C(CH.sub.3).sub.2 CH.sub.2 !. Also described are methods for forming such allenic phosphonates from ethynyl-.beta.-ionol, and for converting these allenic compounds to allylic phosphonate compounds which can be used in the synthesis of a variety of biologically-active materials.
Claims19
An allenic phosphonate compound of the formula:
- ##STR11## wherein R and R'=C.sub.1 -C.sub.4 alkyl groups, or R, R'=(CH.sub.2).sub.n (n=2 or 3) or CH.sub.2 C(CH.sub.3).sub.2 CH.sub.2 !.
A method of preparing an allenic phosphonate compound of the formula:
- ##STR12## wherein R and R'=C.sub.1 -C.sub.4 alkyl groups, or R, R'=(CH.sub.2).sub.n (n=2 or 3) or CH.sub.2 C(CH.sub.3).sub.2 CH.sub.2 !
- comprising the steps:
- (I) forming a reaction mixture in an aprotic solvent comprising:
- (a) ethynyl-.beta.-ionol;
- (b) at least one molar equivalent of a non-nucleophilic base;
- and
- (c) at least one molar equivalent of a chlorophosphite reagent of the formula, (RO).sub.2 PCl, wherein the R groups independently represent C.sub.1 to C.sub.4 alkyl or wherein the R groups, taken together, form part of a 5- or 6-member ring;
- and
- (II) maintaining said reaction mixture until said allenic phosphonate is formed.
A method of preparing a C-15 allylic phosphonate compound of the formula:
- ##STR13## wherein R and R'=C.sub.1 -C.sub.4 alkyl groups comprising the steps:
- (I) forming a first reaction mixture in an aprotic solvent comprising:
- (a) ethynyl-.beta.-ionol;
- (b) at least one molar equivalent of a non-nucleophilic base;
- and
- (c) at least one molar equivalent of a chlorophosphite reagent of the formula, (RO).sub.2 PCl, wherein the R groups independently represent C.sub.1 to C.sub.4 alkyl or wherein the R groups, taken together, form part of a 5- or 6-member ring;
- (II) maintaining said first reaction mixture until an allenic phosphonate is formed;
- (III) forming a second reaction mixture in an alcohol solvent comprising the allenic phosphonate of step II, ammonium formate, and 10% Pd-C;
- and
- (IV) vigorously agitating said second reaction mixture while heating it to a temperature in excess of room temperature.
Dependencies are inferred from the claim text.