Catalytic synthesis of vitamin A intermediate
US-9040742-B2 · May 26, 2015 · US
US9309194B2 · US · B2
| Field | Value |
|---|---|
| Publication number | US-9309194-B2 |
| Application number | US-201214128802-A |
| Country | US |
| Kind code | B2 |
| Filing date | Jun 14, 2012 |
| Priority date | Jun 22, 2011 |
| Publication date | Apr 12, 2016 |
| Grant date | Apr 12, 2016 |
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The present invention relates to compounds of formula (I) wherein R 1 signifies a C 1 -C 15 alkyl moiety or a C 2 to C 18 alkenyl moiety, to their process of production as well as to their use in organic synthesis, especially as intermediates (building blocks) in the synthesis of vitamin A or β-carotene or derivatives thereof, or other carotenoids, e.g. canthaxanthin, astaxanthin or zeaxanthin, preferably vitamin A.
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The invention claimed is: 1. A compound of formula (I): wherein R 1 signifies a C 1 -C 15 alkyl moiety or a C 2 -C 18 is alkenyl moiety. 2. The compound according to claim 1 , wherein R 1 is a linear C 1 -C 15 alkyl moiety. 3. The compound according to claim 1 , wherein R 1 is methyl, ethyl or pentadecyl. 4. The compound according to claim 1 , wherein R 1 is an unbranched C 2 -C 18 alkenyl moiety having more than three C-C double bonds. 5. The compound according to claim 1 , wherein the compound of formula (I) is a pure stereoisomeric form. 6. The compound according to claim 1 , wherein the compound of formula (I) is a mixture of stereoisomeric forms. 7. A process for production of a compound of formula (I) according to claim 1 , wherein the process comprises reducing, in the presence of 2-methyl-CBS-oxazaborolidine and borane dimethyl sulphide, a compound of formula (II): wherein R 1 signifies a C 1 -C 15 alkyl moiety or a C 2 -C 18 alkenyl moiety.
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