Synthesis of terfenadine and derivatives
AssigneeSepracor Inc.
InventorsChris Hugh Senanayake, Qun Kevin Fang, Scott Harold Wilkinson
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Abstract
Processes for preparing compounds having the general formula: ##STR1## wherein R.sup.1a is protected carboxy, carboxy, hydroxymethyl, protected hydroxymethyl, or methyl are disclosed. Processes of the invention begin with a starting material of the general formula IV ##STR2## wherein R.sup.1 and R.sup.2 are as defined in the specification.
Claims8
A compound of Formula VI ##STR31## wherein R.sup.1 is chosen from the group consisting of ##STR32## wherein D represents the residue of a 5- or 6-membered, saturated or aromatic ring;
- R.sup.2 is chosen from hydrogen, trialkylsilyl, benzyl, tetrahydropyran-2-yl, lower-alkylcarbonyl, arylcarbonyl and arylmethyl, wherein the aryl group is phenyl optionally substituted with from one to three substituents each independently selected from the group consisting of lower alkyl, lower alkoxy, and halo;
- R.sup.3 is chosen from alkoxy, wherein the alkoxy group contains from one to about 8 carbon atoms;
- alkenyloxy, wherein the alkenyloxy group contains from one to about 4 carbon atoms;
- arylmethoxy, wherein the aryl group is phenyl optionally substituted with from one to three substituents each independently selected from the group consisting of lower alkyl, lower alkoxy, and halo;
- and --NR.sup.6 R.sup.7 ;
- R.sup.4 is chosen from trialkylsilyl, Li.sup.+, benzyl, tetrahydropyran-2-yl, lower-alkylcarbonyl, arylcarbonyl and arylmethyl, wherein the aryl group is phenyl optionally substituted with from one to three substituents each independently selected from the group consisting of lower alkyl, lower alkoxy, and halo;
- R.sup.5 is alkyl of 1 to 6 carbons;
- and
- R.sup.6 and R.sup.7 are chosen independently from hydrogen, alkyl of 1 to 8 carbons and benzyl.
A process of using a compound of formula VI ##STR33## comprising reducing said compound of formula VI with a hydride or by catalytic hydrogenation to provide a compound of formula I ##STR34## wherein R.sup.1 is chosen from the group consisting of ##STR35## wherein D represents the residue of a 5- or 6-membered, saturated or aromatic ring;
- R.sup.2 is chosen from hydrogen, trialkylsilyl, benzyl, tetrahydropyran-2-yl, lower-alkylcarbonyl, arylcarbonyl and arylmethyl, wherein the aryl group is phenyl optionally substituted with from one to three substituents each independently selected from the group consisting of lower alkyl, lower alkoxy, and halo;
- R.sup.3 is chosen from alkoxy, wherein the alkoxy group contains from one to about 8 carbon atoms;
- alkenyloxy, wherein the alkenyloxy group contains from one to about 4 carbon atoms;
- arylmethoxy, wherein the aryl group is phenyl optionally substituted with from one to three substituents each independently selected from the group consisting of lower alkyl, lower alkoxy, and halo;
- and --NR.sup.6 R.sup.7 ;
- R.sup.4 is chosen from trialkylsilyl, Li.sup.+, benzyl, tetrahydropyran-2-yl, lower-alkylcarbonyl, arylcarbonyl and arymethyl, wherein the aryl group is phenyl optionally substituted with from one to three substituents each independently selected from the group consisting of lower alkyl, lower alkoxy, and halo;
- R.sup.5 is alkyl of 1 to 6 carbons;
- R.sup.6 and R.sup.7 are chosen independently from hydrogen, alkyl of 1 to 8 carbons and benzyl.
Dependencies are inferred from the claim text.