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AssigneeWarner-Lambert Company
InventorsDonald E. Butler, Carl F. Deering, Alan Millar, Thomas N. Nanninga, Bruce D. Roth
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An improved process for the preparation of trans-6-[2-(substituted-pyrrol-1-yl)alkyl]pyran-2-ones by a novel synthesis is described where 1,6-heptadien-4-ol is converted in eight operations to the desired products, as well as an improved process for the preparation of (2R-trans) and trans-(.+-.)-5-(4-fluorophenyl)-2-(1-methylethyl)-N,4-diphenyl-1-[2-(tetra hydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl]1H-pyrrole-3-carboxamide by a novel synthesis where 4-methyl-3-oxo-N-phenylpentanamide is converted in eight operations to the desired product or alternatively 4-fluoro-.alpha.-[2-methyl-1-oxopropyl]-.gamma.-oxo-N,.beta.-diphenylbenze nebutaneamide is converted in one step to the desired product, and additionally, a process for preparing (2R-trans)-5-(4-fluorophenyl)-2-(1-methylethyl)-N,4-diphenyl-1-[2-(tetrahy dro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl]-1H-pyrrole-3-carboxamide from (R)-4-cyano-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]butanoic acid, as well as other valuable intermediates used in the processes.
A compound of Formula V ##STR48## wherein R.sub.7 and R.sub.8 are independently hydrogen, alkyl of from one to three carbon atoms, phenyl or R.sub.7 and R.sub.8 are taken together as --(CH.sub.2).sub.n --, wherein n is 4 or 5, and R.sub.9 is alkyl of from one to eight carbon atoms, a three- to six-membered cycloalkyl group, or .alpha.,.alpha.-dimethylbenzyl.
A compound of Formula VI ##STR49## wherein R.sup.7 and R.sup.8 are independently hydrogen, alkyl of from one to three carbon atoms, phenyl or R.sub.7 and R.sub.8 are taken together as --(CH.sub.2).sub.n --, wherein n is 4 or 5.
A compound of Formula VII ##STR50## wherein R.sub.7 and R.sub.8 are independently hydrogen, alkyl of from one to three carbon atoms, phenyl or R.sub.7 and R.sub.8 are taken together as --(CH.sub.2).sub.n --, wherein n is 4 or 5.
A compound of Formula VIII ##STR51## wherein R.sub.7 and R.sub.8 are independently hydrogen, alkyl of from one to three carbon atoms, phenyl or R.sub.7 and R.sub.8 are taken together as --(CH.sub.2).sub.n --, wherein n is 4 or 5.
Dependencies are inferred from the claim text.