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US 10,370,314 B2Granted
Selective reduction of esters to alcohols
AssigneeDms IP Assets B.V.
InventorsMatthias Beller, Werner Bonrath, Johannes Gerardus De Vries, Yuting Fan, Sandra Hinze, Laurent Lefort, Jonathan Alan Medlock, Pim Puylaert, Richard Van Heck
Life of this patent
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Abstract
The present invention relates to a selective reduction of esters to their corresponding alcohols.
Claims12
A process of production of a compound of formula (II):
- wherein
- R1 is an aromatic ring system which is unsubstituted or an aromatic ring system which is substituted;
- a heteroaromatic ring system which is unsubstituted or a heteroaromatic ring system which is substituted;
- an aliphatic ring system which is unsubstituted or an aliphatic ring system which is substituted;
- —CH3;
- —CH2CH3;
- an unsubstituted C3-C22 alkyl group, which can be linear or branched and which can also be partially unsaturated;
- or a substituted C2-C22 alkyl group, which can be linear or branched and which can also be partially unsaturated, wherein
- the process comprises conducting a selective reduction of a compound of formula (I):
- wherein
- R is a linear C1-C6-alkyl group, which can be substituted;
- a branched C3-C6-alkyl group, which can be substituted or a benzyl group, which can be substituted, and
- R1 is an aromatic ring system which is unsubstituted or an aromatic ring system which is substituted;
- a heteroaromatic ring system which is unsubstituted or a heteroaromatic ring system which is substituted;
- an aliphatic ring system which is unsubstituted or an aliphatic ring system which is substituted;
- —CH3;
- —CH2CH3;
- an unsubstituted C3-C22 alkyl group, which can be linear or branched and which can also be partially unsaturated;
- or a substituted C2-C22 alkyl group, which can be linear or branched and which can also be partially unsaturated, or
- R and R1 form together a 4 to 7 membered ring system, which can be substituted, and wherein
- the selective reduction is carried out in the presence of at least one transition metal catalyst of formula (III):
- [M(L)(X)a(L′)b] (III), wherein
- M is a transition metal and
- X is an anion, and
- L′ is a monodentate ligand, and
- L is a tridentate ligand of formula (IV):
- wherein
- R3 is a linear C1-C4 alkyl group, which can be substituted;
- a branched C3-C4 alkyl group, which can be substituted;
- or a phenyl group, which can be substituted,
- R4 is H;
- a linear C1-C4 alkyl group, which can be substituted;
- a branched C3-C4 alkyl group, which can be substituted;
- or OC1-C2alkyl,
- R5 is H;
- a linear C1-C4 alkyl group, which can be substituted;
- a branched C3-C4 alkyl group, which can be substituted;
- or OC1-C2alkyl, or
- R4 and R5 form a C4-C8 ring system, which can be aliphatic or aromatic, and
- R6 is H;
- a linear C1-C4 alkyl group, which can be substituted;
- a branched C3-C4 alkyl group, which can be substituted;
- or OC1-C2alkyl,
- R7 is H;
- a linear C1-C4 alkyl group, which can be substituted;
- a branched C3-C4 alkyl group, which can be substituted;
- or OC1-C2alkyl,
- R8 is H or a linear C1-C4 alkyl group, which can be substituted;
- a branched C3-C4 alkyl group, which can be substituted,
- R9 is —CH3 or —CH2CH3,
- m is 0, 1 or 2, and
- n is 0, 1 or 2,
- with the proviso that the sum of m+n is 1 or 2,
- o is 2 or 3,
- a is 0, 1, 2, or 3, and
- b is 0, 1, 2, or 3,
- with the proviso that the sum of a+b is 2, 3 or 4.
54 more elements
Dependencies are inferred from the claim text.