EP3898583A1 - Specific ?,?-unsaturated carboxylates - Google Patents
Specific ?,?-unsaturated carboxylatesInfo
- Publication number
- EP3898583A1 EP3898583A1 EP19818116.6A EP19818116A EP3898583A1 EP 3898583 A1 EP3898583 A1 EP 3898583A1 EP 19818116 A EP19818116 A EP 19818116A EP 3898583 A1 EP3898583 A1 EP 3898583A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- formula
- compounds
- process according
- compound
- catalyst
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 150000007942 carboxylates Chemical class 0.000 title abstract description 6
- 150000001875 compounds Chemical class 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 239000003054 catalyst Substances 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- -1 carboxylate esters Chemical class 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 125000000746 allylic group Chemical group 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 239000000758 substrate Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- NDGRVUREWSEVSY-UHFFFAOYSA-N 3-methyl-1-(2,6,6-trimethylcyclohexen-1-yl)pent-1-en-4-yn-3-ol Chemical compound CC1=C(C=CC(C)(O)C#C)C(C)(C)CCC1 NDGRVUREWSEVSY-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 239000012300 argon atmosphere Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 229910052707 ruthenium Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- OPSSCPNCFKJCFR-UHFFFAOYSA-N 3-methyl-5-(2,6,6-trimethylcyclohexen-1-yl)penta-2,4-dienal Chemical compound O=CC=C(C)C=CC1=C(C)CCCC1(C)C OPSSCPNCFKJCFR-UHFFFAOYSA-N 0.000 description 1
- 238000006418 Brown reaction Methods 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- JIMXXGFJRDUSRO-UHFFFAOYSA-N adamantane-1-carboxylic acid Chemical compound C1C(C2)CC3CC2CC1(C(=O)O)C3 JIMXXGFJRDUSRO-UHFFFAOYSA-N 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000006462 rearrangement reaction Methods 0.000 description 1
- 229960000342 retinol acetate Drugs 0.000 description 1
- QGNJRVVDBSJHIZ-QHLGVNSISA-N retinyl acetate Chemical compound CC(=O)OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C QGNJRVVDBSJHIZ-QHLGVNSISA-N 0.000 description 1
- 235000019173 retinyl acetate Nutrition 0.000 description 1
- 239000011770 retinyl acetate Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
- C07C403/06—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by singly-bound oxygen atoms
- C07C403/12—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by singly-bound oxygen atoms by esterified hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/56—Ring systems containing bridged rings
- C07C2603/58—Ring systems containing bridged rings containing three rings
- C07C2603/70—Ring systems containing bridged rings containing three rings containing only six-membered rings
- C07C2603/74—Adamantanes
Definitions
- the present invention relates to specific a,b-unsaturated carboxylates and a method of making them.
- Ri is a Ci - C -alkyl moiety, preferably -CH 3 or -CH 2 CH 3 , and
- R 3 is one of the following groups
- R 4 is CH 3 or phenyl
- Vitamin A acetate via a reduction followed by an acetylation
- Ri is a Ci - C4-alkyl moiety, preferably -CH3 or -CH 2 CH3, and
- R 3 is one of the following groups
- R is CH 3 or phenyl
- Ri is-CHs or -CH 2 CH 3 .
- the present invention relates to compounds of formula (la), which are compound of formula (I), wherein Ri is-CH 3 or -Ch CH !
- R 3 is one of the following groups Therefore the present invention relates to compounds of formula (lc), which are compounds of formula (I), (la) or (lb), wherein
- R 3 is one of the following groups
- the compounds according to the present invention are produced using commonly known processes.
- a compound of formula (II) having a terminal C-C triple bond is reacted with a specific carboxylic acid.
- the substituents Ri , R 2 and R 3 have the same meanings (and the same preferred meanings) as defined above.
- R5, Re, R7, and Rs signify -CH3, -OCH3, -NO 2 , halogen or -H, and
- X and Y signify independently from each other an allylic moiety
- q signifies an integer 1 , 2 or 3.
- a very preferred catalyst is the one of formula (IVa)
- the substrate (Compound of formula (II) to catalyst ratio (mol-based) is usually from 5000 : 1 to 10 : 1 , preferably from 1000 : 1 to 20 : 1.
- the process according to the present invention is carried out without any solvents or in at least one apolar aprotic organic solvent. All reactants are added together and mixed. The reaction mixture is heated to the temperature at which the transition metal-based catalytic rearrangement reaction occurs, to provide a resulting mixture.
- paraffin oil a mixture of saturated aliphatic hydrocarbons
- carboxylate esters such as ethyl acetate.
- the process according to the present invention is usually carried out under very mild reaction condition.
- the reaction temperature is usually between -5°C and 60°C. Preferably between 0° and 50°C.
- Example illustrates the invention further without limiting it. All per-centages and parts, which are given, are related to the weight and the tempera-tures are given in °C, when not otherwise stated.
- Example 1 3-Methyl-1-(2,6,6-trimethylcyclohex-1 -en-1 -yl)pent-1-en-4-yn-3-ol (2.33 g, 10 mmol) and 1- adamantanecarboxylic acid (2.73 g, 15 mmol, 1.5 eq.) were dissolved in anhydrous ethyl acetate (10 mL) under argon atmosphere. In a counter flow of argon, 61 mg (0.1 mmol, 1.0 mol%) of the ruthenium catalyst of formula (IVa) were added. After stirring for 3 h at 20°C , the light yellow-brown reaction mixture was concentrated under reduced pressure (rotavap, 20°C water-bath temperature). The crude product was dried for another 2 h at 20 mbar resulting in a light brown oil.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention relates specific α,β-unsaturated carboxylates and a method of making them.
Description
SPECIFIC a.B-UNSATURATED CARBOXYLATES
The present invention relates to specific a,b-unsaturated carboxylates and a method of making them.
The specific a, b-unsaturated carboxylates which are aimed to be produced are represented by the following formula (I)
wherein
Ri is a Ci - C -alkyl moiety, preferably -CH3 or -CH2CH3, and
R3 is one of the following groups
wherein
R4 is CH3 or phenyl
(the * is showing where the bond is localized).
These specific a,b-unsaturated carboxylates are useful compounds. They can be used as such or they are useful intermediates to produce other compounds. For example compound (la)
is used as an intermediate in the production of Vitamin A acetate (via a reduction followed by an acetylation)
Therefore due to the importance of such important intermediates, there is always a need for improved methods of producing such compounds.
The compounds of formula (I) are not known from the prior art.
Therefore the present invention relates to compounds of formula (I)
wherein
Ri is a Ci - C4-alkyl moiety, preferably -CH3 or -CH2CH3, and
(the * is showing where the bond is localized), and
R3 is one of the following groups
wherein
R is CH3 or phenyl
(the * is showing where the bond is localized).
Preferred are compounds of formula (I), wherein
Ri is-CHs or -CH2CH3.
Therefore the present invention relates to compounds of formula (la), which are compound of formula (I), wherein Ri is-CH3 or -Ch CH !
Preferred are compounds of formula (I), wherein
Therefore the present invention relates to compounds of formula (lb), which are compounds of formula (I) or (la), wherein
Preferred are compounds of formula (I), wherein
R3 is one of the following groups
Therefore the present invention relates to compounds of formula (lc), which are compounds of formula (I), (la) or (lb), wherein
R3 is one of the following groups
Most preferred are the following compound of formulae (G) to (I””)
The compounds according to the present invention are produced using commonly known processes.
A preferred process to produce these compounds is the following
A compound of formula (II) having a terminal C-C triple bond is reacted with a specific carboxylic acid. The substituents Ri , R2 and R3 have the same meanings (and the same preferred meanings) as defined above.
The reaction is carried in the presence of a specific catalyst (Cat) which has the following formula (IV)
wherein
R5, Re, R7, and Rs signify -CH3, -OCH3, -NO2, halogen or -H, and
X and Y signify independently from each other an allylic moiety, and
q signifies an integer 1 , 2 or 3.
A very preferred catalyst is the one of formula (IVa)
The substrate (Compound of formula (II) to catalyst ratio (mol-based) is usually from 5000 : 1 to 10 : 1 , preferably from 1000 : 1 to 20 : 1.
The process according to the present invention is carried out without any solvents or in at least one apolar aprotic organic solvent. All reactants are added together and mixed. The reaction mixture is heated to the temperature at which the transition metal-based catalytic rearrangement reaction occurs, to provide a resulting mixture.
As solvents there can be used in the scope of the present invention in general apolar aprotic organic solvents, especially aliphatic, cyclic and aromatic hydrocarbons, such as, for example, C7-Cio-alkanes, C5-C7-cycloalkanes, benzene, toluene and naphthalene as well as mixtures of such solvents with one another, e.g. paraffin oil (a mixture of saturated aliphatic hydrocarbons). As well as carboxylate esters, such as ethyl acetate. The process according to the present invention is usually carried out under very mild reaction condition. The reaction temperature is usually between -5°C and 60°C. Preferably between 0° and 50°C.
The following Example illustrates the invention further without limiting it. All per-centages and parts, which are given, are related to the weight and the tempera-tures are given in °C, when not otherwise stated.
Examples
Example 1 : 3-Methyl-1-(2,6,6-trimethylcyclohex-1 -en-1 -yl)pent-1-en-4-yn-3-ol (2.33 g, 10 mmol) and 1- adamantanecarboxylic acid (2.73 g, 15 mmol, 1.5 eq.) were dissolved in anhydrous ethyl acetate (10 mL) under argon atmosphere. In a counter flow of argon, 61 mg (0.1 mmol, 1.0 mol%) of the ruthenium catalyst of formula (IVa) were added. After stirring for 3 h at 20°C , the light yellow-brown reaction mixture was concentrated under reduced pressure (rotavap, 20°C water-bath temperature). The crude product was dried for another 2 h at 20 mbar resulting in a light brown oil.
The product of formula (I””)
Example 2: 3-Methvl-5-(2, 6, 6-trimethylcyclohex- 1 -enyl) penta-2, 4-dienal
3-Methyl-1-(2,6,6-trimethylcyclohex-1 -en-1 -yl)pent-1-en-4-yn-3-ol (2.26 g, 10 mmol) and 2,2-dimethylpropanoic acid (1.53 g, 15 mmol, 1.5 eq.) were mixed under argon atmosphere. In a counter flow of argon, 122 mg (0.2 mmol, 2.0 mol%) of the ruthenium catalyst of formula (IVa) were added. After stirring for 18 h at 20 °C, 20 ml of ethyl acetate and 10 % sulfuric acid (150 mI_) were added drop wise. After one hour at 24 °C the reaction was complete and the reaction mixture was washed once with semi saturated sodium bicarbonate (80 mL) and once with water (40 mL). The aqueous layers were re-extracted twice with ethyl acetate (40 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated under reduced pressure (rotavap, 30 °C water-bath temperature). The crude product compound of formula (I’”)
was dried for another 2 h at 20 mbar resulting in a red-brown oil (2.76 g, 74 % purity, 94 % yield). In the following table more compounds of formula (I) have been produced by the same way as in Example 1 and 2. Other carboxylic acids have been used and/or the reaction time and/or the reaction temperature and/or the amount of ethyl acetate (solvent) have been varied. Table 1 :
Claims
1. Compounds of formula (I)
wherein
R3 is one of the following groups
wherein
R4 is CH3 or phenyl
(the * is showing where the bond is localized).
2. Compounds according to claim 1 , wherein
Ri is-CH3 or -CH2CH3.
3. Compounds according to claim 1 or claim 2, wherein
4. Compounds according to any of the preceding claims, wherein R3 is one of the following groups
5. Compounds according to any of the preceding claims, having the formula (G) to (I””)
6. Process to produce the compounds as defined in any of claims 1 - 5, wherein a compound of formula (II)
is reacted with a compound of formula (III)
wherein the Ri , R2 and R3 have the same meanings as defined above in the presence of at least one catalyst of formula (IV)
wherein
R5, Re, R7, and R8 signify -CH3, -OCH3, -N02, halogen or -H,, and X and Y signify independently from each other an allylic moiety, and q signifies an integer 1 , 2 or 3.
7. Process according to claim 6, wherein a catalyst of formula (IVa)
is used.
8. Process according to claim 6 or 7, wherein the substrate (compound of formula (II)) to catalyst ratio (mol-based) is usually from 5000 : 1 to 10 : 1 , preferably from 1000 : 1 to 20 :
1.
9. Process according to any of claims 6 to 8, wherein the process is carried out without any solvents.
10. Process according to any of claims 6 to 8, wherein the process is carried out in at least one apolar aprotic organic solvent.
11. Process according to claim 10, wherein the solvent is chosen from the group consisting of, aliphatic, cyclic and aromatic hydrocarbons, and carboxylate esters.
12. Process according to any of claims 6 to 1 1 , wherein the process is carried out at a temperature of from -5°C to 60°C.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP18214434 | 2018-12-20 | ||
| PCT/EP2019/085500 WO2020127160A1 (en) | 2018-12-20 | 2019-12-17 | SPECIFIC α,β-UNSATURATED CARBOXYLATES |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP3898583A1 true EP3898583A1 (en) | 2021-10-27 |
Family
ID=65010418
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP19818116.6A Pending EP3898583A1 (en) | 2018-12-20 | 2019-12-17 | Specific ?,?-unsaturated carboxylates |
Country Status (3)
| Country | Link |
|---|---|
| EP (1) | EP3898583A1 (en) |
| CN (1) | CN113242852A (en) |
| WO (1) | WO2020127160A1 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115698028B (en) * | 2020-06-19 | 2025-02-18 | 帝斯曼知识产权资产管理有限公司 | Improved process for producing specific alpha, beta-unsaturated carboxylic acid esters |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2282480T3 (en) * | 2001-10-31 | 2007-10-16 | Dsm Ip Assets B.V. | RETINOID PREPARATION. |
| CN104478928B (en) * | 2014-12-25 | 2017-03-15 | 中国农业大学 | The α that a kind of α diphenylphosphines replace, β unsaturated carboxylic ester compounds and its preparation and application method |
-
2019
- 2019-12-17 WO PCT/EP2019/085500 patent/WO2020127160A1/en not_active Ceased
- 2019-12-17 CN CN201980084496.6A patent/CN113242852A/en active Pending
- 2019-12-17 EP EP19818116.6A patent/EP3898583A1/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| CN113242852A (en) | 2021-08-10 |
| WO2020127160A1 (en) | 2020-06-25 |
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