(6r,10r)-6,10,14-trimetylpentadecan-2-one prepared from 6,10-dimetylundec-5-en-2-one or 6,10-dimetylundeca-5,9-dien-2-one
AssigneeDsm IP Assets B.V.
InventorsWerner BONRATH, Thomas NETSCHER, Jonathan Alan MEDLOCK, René Tobias STEMMLER, Johannes TSCHUMI, Gerardus Karel Maria VERZIJL, Andreas Hendrikus Maria DE VRIES
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Abstract
The present invention relates to a process of manufacturing (6R,10R)-6,10,14-trimetylpentadecan-2-one in a multistep synthesis from 6,10-dimetylundec-5-en-2-one or 6,10-dimetylundeca-5,9-dien-2-one. The process is very advantageous in that it forms in an efficient way the desired chiral product from a mixture of stereoisomers of the starting product.
Claims16
A process of manufacturing (6R,10R)-6,10,14-trimethylpentadecan-2-one in a multistep synthesis from 6,10-dimethylundec-5-en-2-one or 6,10-dimethylundeca-5,9-dien-2-one comprising the steps
- a) providing a mixture of (E)-6,10-dimethylundec-5-en-2-one and (Z)-6,10-dimethylundec-5-en-2-one or a mixture of (E)-6,10-dimethylundeca-5,9-dien-2-one and (Z)-6,10-dimethylundeca-5,9-dien-2-one;
- b) separating one isomer of 6,10-dimethylundec-5-en-2-one or of 6,10-dimethylundeca-5,9-dien-2-one from the mixture of step a)
- c) asymmetric hydrogenation using molecular hydrogen in the presence of a chiral iridium complex and yielding (R)-6,10-dimethylundecan-2-one;
- d) chemically transforming (R)-6,10-dimethylundecan-2-one to a mixture of (R,E)-6,10,14-trimethylpentadec-5-en-2-one and (R,Z)-6,10,14-trimethylpentadec-5-en-2-one;
- e) separating one isomer of (R)-6,10,14-trimethylpentadec-5-en-2-one from the mixture obtained in step d)
- f) asymmetric hydrogenation using molecular hydrogen in the presence of a chiral iridium complex and yielding (6R,10R)-6,10,14-trimethylpentadecan-2-one;
- wherein the steps a)-f) are in the order a, b, c, d, e, f.
Composition comprising
- at least one ketal of formula (XI) or (XII) and
- at least one chiral iridium complex
- wherein a wavy line represents a carbon-carbon bond which is linked to the adjacent carbon-carbon double bond so as to have said carbon-carbon double bond either in the Z or in the E-configuration;
- and wherein the double bond having dotted lines () in formula represent either a single carbon-carbon bond or a double carbon-carbon bond;
- and wherein represents a stereogenic centre;
- and wherein
- Q1 and Q2
- stand either individually or both for a C1-C10 alkyl group or a halogenated C1-C10 alkyl group;
- or form together a C2-C6 alkylene group or a C6-C8 cycloalkylene group.
Ketal of formula (XX-A) or (XX-B) or (XX-C) or (XX-D)
- wherein the double bond having dotted lines () in the above formulae represents either a single carbon-carbon bond or a double carbon-carbon bond;
- and
- wherein a wavy line represents a carbon-carbon bond which is linked to an adjacent single carbon bond ( representing ) or to an adjacent carbon-carbon double bond ( representing ) so as to have said carbon-carbon double bond either in the Z or in the E-configuration.
Dependencies are inferred from the claim text.