Claims
- 1. A process for preparing substituted cyclohexanoic acids of formula (I) where Ra is a carbon-containing group optionally linked by oxygen, sulfur or nitrogen to the phenyl ring and j is 1-5; andone of R and R* is hydrogen and the other is C(O)OH; which process comprises: catalytically reducing a ketone of formula II where alkyl has 1-6 carbon atoms and (Ra)j is the same as defined above, using a heavy metal catalyst and hydrogen gas.
- 2. The process of claim 1 wherein j is 2 and the Ra groups are substituted at the 3 and 4 positions on the phenyl ring.
- 3. The process of claim 1 wherein the compound is a compound of formula wherein:R1 is —(CR4R5)rR6 wherein the alkyl moieties are unsubstituted or substituted with one or more halogens; R4 and R5 are independently selected hydrogen or C1-2 alkyl; R6 is hydrogen, methyl, hydroxyl, aryl, halo substituted aryl, aryloxyC1-3 alkyl, halo substituted aryloxyC1-3 alkyl, indanyl, indenyl, C7-11 polycycloalkyl, tetrahydrofuranyl, furanyl, tetrahydropyranyl, pyranyl, tetrahydrothienyl, thienyl, tetrahydrothiopyranyl, thiopyranyl, C3-6 cycloalkyl, or a C4-6 cycloalkyl, containing one or two unsaturated bonds, wherein the cycloalkyl or heterocyclic moiety is unsubstituted or substituted by 1 to 3 methyl groups, one ethyl group, or an hydroxyl group; provided that: b) when R6 is hydroxyl, then r is 2 to 6; or d) when R6 is 2-tetrahydropyranyl, 2-tetrahydrothiopyranyl, 2-tetrahydrofuranyl, or 2-tetrahydrothienyl, then r is 1 to 6; X is YR2; Y is O; X2 is O; R2 is —CH3 or —CH2CH3, unsubstituted or substituted by 1 or more halogens; one of R and R* is hydrogen and the other is C(O)OH.
- 4. The process of claim 1 wherein the heavy metal catalyst is platinum oxide.
- 5. The process of claim 3 wherein in formula (I) R1 is —CH2-cyclopropyl, cyclopentyl, 3-hydroxycyclopentyl, methyl or CHF2 and R2 is CF2H or CH3.
- 6. The process of claim 3 wherein R1 is cyclopentyl and R2 is methyl.
Parent Case Info
This application is a 371 of PCT/US00/25379 filed Sep. 15, 2000 which claim s benefit of US provisional application 60/154,084 filed Sep. 15, 1999.
PCT Information
Filing Document |
Filing Date |
Country |
Kind |
PCT/US00/25379 |
|
WO |
00 |
Publishing Document |
Publishing Date |
Country |
Kind |
WO01/19785 |
3/22/2001 |
WO |
A |
Foreign Referenced Citations (3)
Number |
Date |
Country |
WO 9503794 |
Feb 1995 |
WO |
WO 9509623 |
Apr 1995 |
WO |
WO9524381 |
Sep 1995 |
WO |
Non-Patent Literature Citations (1)
Entry |
Agami et al, Kinetics and Mechanism of the Conjugate Hydrocyanation of alpha, beta -Unsaturated Ketones by the Potassium Cyanide-Ammonium Chloride System, 1982, Journal of Organic Chemistry, 47, pp. 3561-3563. |
Provisional Applications (1)
|
Number |
Date |
Country |
|
60/154084 |
Sep 1999 |
US |