6-chromanol derivatives and their synthesis
AssigneeDsm IP Assets B.V.
InventorsRaphael Beumer, Werner Bonrath, Jan-Marc Delpho, Marcel Joray, Jonathan Alan Medlock, Thomas Netscher, Domenico Soriano, René Tobias Stemmler
Life of this patent
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Abstract
The present invention relates to novel compounds which are particularly useful for the synthesis of novel chromanol derivatives. These compounds have interesting properties. Particularly, the novel chromanol derivatives have interesting antioxidant properties as well as flavours and fragrances.
Claims18
A compound of formula (I):
- wherein R1, R3 and R4 represent independently from each other hydrogen or methyl groups;
- R2 represents hydrogen or R2′ which is a phenol protecting group;
- and wherein each * marks a chiral/stereogenic centre, and # marks a chiral/stereogenic centre.
A compound of formula (IV):
- wherein each * marks a chiral/stereogenic centre.
A process of manufacturing a compound of formula (IV):
- comprising the step of:
- d) hydrogenating a compound of formula (VI):
- to yield the compound of formula (IV), wherein the dotted line indicates a carbon-carbon double bond which is located at one of the two indicated positions.
A compound of formula (VI):
- wherein the dotted line indicates a carbon-carbon double bond which is located at one of the two indicated positions;
- and wherein
- each * marks a chiral/stereogenic centre.
A compound of formula (VII):
- wherein the dotted line indicates a carbon-carbon double bond which is located at one of the two indicated positions;
- and wherein
- each * marks a chiral/stereogenic centre.
A process of manufacturing the compound of formula (II-A):
- comprising the step
- b) providing a compound of formula (IV):
- followed by the steps of either:
- c1) ethinylating the compound of formula (IV) using ethyne in the presence of a basic substance to yield a compound of formula (V):
- c2) hydrogenating the compound of formula (V) with molecular hydrogen in the presence of a Lindlar catalyst to yield the compound of formula (II-A);
- or
- c3) vinylating the compound of formula (IV) by addition of a vinyl Grignard reagent to yield the compound of formula (II-A);
- wherein
- each * marks a chiral/stereogenic centre.
A compound of formula (V):
- wherein each * marks a chiral/stereogenic centre.
A compound of formula (II-A):
- wherein each * marks a chiral/stereogenic centre.
A process of manufacturing the compound of formula (II-B):
- wherein the process comprising conducting isomerization of a compound of formula (II-A):
- wherein each * marks a chiral/stereogenic centre;
- and wherein
- the wavy line represents a carbon-carbon bond which when linked to the carbon-carbon double bond is either in the Z- or in the E-configuration.
A compound of formula (II-B):
- wherein each * marks a chiral/stereogenic centre;
- and wherein
- the wavy line represents a carbon-carbon bond which when linked to the carbon-carbon double bond is either in the Z- or in the E-configuration.
A process of manufacturing a compound of formula (I-A) comprising the steps of:
- b1) providing a compound of formula (II-A) or (II-B):
- b2) condensing the compound of formula (II-A) or (II-B) with a compound of formula (III) to yield the compound of formula (IA)
- wherein R1, R3 and R4 represent independently from each other hydrogen or methyl groups;
- and wherein
- each * marks a chiral/stereogenic centre, and # marks a chiral/stereogenic centre;
- and wherein
- the wavy line represents a carbon-carbon bond which when linked to the carbon-carbon double bond is either in the Z- or in the E-configuration.
A process of manufacturing a compound of formula (I-B) comprising the steps of:
- a1) providing a compound of formula (I-A):
- a2) reacting the compound of formula (I-A) with a protecting agent to yield the compound of formula (I-B):
- wherein R1, R3 and R4 represent independently from each other hydrogen or methyl groups;
- and
- R2′ represents a phenol protecting group;
- and wherein
- each * marks a chiral/stereogenic centre, and # marks a chiral/stereogenic centre.
A composition comprising a compound of formula (I) and a compound of formula (XI):
- wherein R1, R3 and R4 represent independently from each other hydrogen or methyl groups;
- R2 represents hydrogen or R2′ which is a phenol protecting group;
- and wherein
- each * marks a chiral/stereogenic centre, and # marks a chiral/stereogenic centre.
A flavour or fragrance composition which comprises the compound of formula (IV), (VI), (VII), (V), (II-A) or (II-B):
- wherein the dotted line indicates a carbon-carbon double bond which is located at one of the two indicated positions;
- and wherein
- each * marks a chiral/stereogenic centre.
Dependencies are inferred from the claim text.