Back to results
US 5,395,953 AGranted
Method of preparing hydrindane compounds and hydrindane-related compounds
AssigneeDuphar International Research B.V.
InventorsMiguel A. Maestro, Antonio Mourino, Benjamin Borsje, Sebastianus J. Halkes
Life of this patent
Estimating the term…
Abstract
The invention relates to a method of preparing a compound having an alkyl or alkoxyalkyl side-chain with a terminal 2-hydroxyprop-2-yl group, by oxidizing a compound having a terminal isopropyl group in its side-chain with a dioxirane as the oxidant.
Claims3
A method of preparing a compound of the general formula ##STR8## wherein R is a methyl group, an ethyl group, a fluorinated ethyl group, a protected hydroxymethyl group or a formyl group;
- R.sub.1 is an alkyl group or alkoxyalkyl group having 3 to 16 carbon atoms, which group is optionally substituted with one or more substituents selected from cyclopropyl and fluorine, and which group has a terminal 2-hydroxyprop-2-yl group;
- Z is a carbonyl group or a protected hydroxymethylene group;
- and
- R.sub.2 is a hydrogen atom;
- or wherein:
- Z and R.sub.2, together with the C-atom to which they are commonly attached, constitute a ring system, comprising one ring or more annelated rings, each ring individually having 3-7 ring atoms of which 1-3 atoms may be heteroatoms selected from N, O and S, and optionally being substituted with a substituent selected from the group consisting of a C.sub.1 -C.sub.3 alkyl group, a protected hydroxy group, a halogen atom, an optionally substituted C.sub.3 -C.sub.7 cycloaliphatic group and optionally substituted phenyl group;
- said method being characterized in that a compound of the general formula ##STR9## wherein R.sub.5 is a methyl group, an ethyl group, a fluorinated ethyl group, a hyroxymethyl group or a protected hydroxymethyl group;
- R.sub.3 is an alkyl group or alkoxyalkyl group having 3 to 16 carbon atoms, which group is optionally substituted with one or more substituents selected from cyclopropyl and fluorine, and which group has a terminal isopropyl group;
- Y is a hydroxymethylene group or a protected hydroxymethylene group;
- and
- R.sub.2 is a hydrogen atom;
- or wherein:
- Y and R.sub.2 together with the C-atom to which they are commonly attached, constitute a ring system, comprising one ring or more annelated rings, each ring individually having 3-7 ring atoms of which 1-3 atoms may be heteroatoms selected from N, O and S, and optionally being substituted with a substituent selected from the group consisting of a C.sub.1 -C.sub.3 alkyl group, a protected hydroxy group, a halogen atom, an optionally substituted C.sub.3 -C.sub.7 cycloaliphatic group and an optionally substituted phenyl group;
- is oxidized in one oxidation step by using a dioxirane selected from the group consisting of dimethyl dioxirane, methyl (trifluoromethyl) dioxirane and bis(trifluoromethyl) dioxirane as the oxidant.
11 more elements
Dependencies are inferred from the claim text.