US 6,583,312 B2Granted

Process for preparing optically active trimethyllactic acid and its esters

AssigneeBayer Aktiengesellschaft

InventorsWolfram Sirges, Claus Dreisbach

Life of this patent

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Abstract

The invention relates to a novel process for preparing optically active trimethyllactic acid and/or its esters by catalytic hydrogenation of trimethylpyruvic acid and/or its esters in the presence of noble metal complex catalysts containing phosphorus ligands.

Claims5

Dependent claims

A process for preparing optically active trimethyllactic acid and/or esters thereof having formula (I)

wherein R1 represents hydrogen, alkyl, aryl, aralkyl, or heterocyclyl, comprising enatiomerically hydrogenating trimethylpyruvic acid and/or esters thereof having formula (II)
wherein R1 has the meanings specified for formula (I),
in the presence of a catalyst comprising one or more noble metal complexes containing optically active bisphosphines as ligands selected from the group consisting of
(1) a bisphosphine of formula (B1)
where
R2 denotes phenyl, 3-methylphenyl, 4-methylphenyl, 3,5-dimethylphenyl, 4-methoxyphenyl, 3,5-dimethyl-4-methoxyphenyl, cyclohexyl, or cyclopentyl, or
(2) a bisphosphine of formula (B2)
where
R3 denotes phenyl, 4-methylphenyl, 3,5-dimethylphenyl, 4-methoxyphenyl, 3,5-dimethyl-4-methoxyphenyl, or cyclohexyl, or
(3) a bisphosphine of formula (B3)
where
R3 denotes phenyl, 4-methylphenyl, 3,5-dimethylphenyl, 4-methoxyphenyl, 3,5-dimethyl-4-methoxyphenyl, or cyclohexyl,
R4 denotes H, methyl, or methoxy,
R5 denotes H, methyl, methoxy, or chlorine, and
R6 denotes methyl, methoxy, or trifluoromethyl, or
(4) a bisphosphine of formula (B4)
where
R7 represents methyl, ethyl, propyl, or isopropyl, or
(5) 2,3-bis(diphenylphosphino)butane of formula (B5)
(6) 1,2-bis(diphenylphosphino)propane of formula (B6)
(7) 5,6-bis(diphenylphosphino)-2-norbornane of formula (B7)
(8) 1-substituted 3,4-bis(diphenylphosphino)pyrrolidine of formula (B8)
(9) 2,4-bis(diphenylphosphino)pentane of formula (B9)
(10) 2,3-O-isopropylidene-2,3-dihydroxy-1,4-bis(diphenylphosphino)butane of formula (B10)
(11) 1,2-bis-[(o-methoxyphenyl)phenylphosphino]ethane of formula (B11)
(12) 1-[1′,2-bis(diphenylphosphino)ferrocenyl]ethanol of formula (B12)
(13) 1-tert-butoxycarbonyl-4-diphenylphosphino-2-diphenylphosphinomethyl-pyrrolidine of formula (B13)
(14) a bisphosphine of formula (B14)
where
R8 denotes phenyl, cyclohexyl, 4-methylphenyl, 4-methoxyphenyl, 3,5-dimethylphenyl, 3,5-dimethyl-4-methoxyphenyl, 4-tert-butyl, or 3,5-di-tert-butyl, or
(15) a ferrocenyldiphosphine of formula (B15)
where
R8 denotes phenyl, cyclohexyl, 4-methylphenyl, 4-methoxyphenyl, 3,5-dimethylphenyl, 3,5-dimethyl-4-methoxyphenyl, 4-tert-butyl, or 3,5-di-tert-butyl, and
R9 denotes C1-C8-alkyl, phenyl, or phenyl monosubstituted to trisubstituted by C1-C4-alkoxy.

31 more elements

Dependencies are inferred from the claim text.

Facts

Application: 09/864,906Filed 24 May 2001
Priority: DE 100 27 15431 May 2000
Published: US 2002/0035271 A121 Mar 2002
Granted: 24 Jun 2003
Term ends: Not estimatedThe source records don’t support an estimate.

Classification3 codes

C07C 51/367
By reactions not involving formation of carboxyl groups: by introduction of functional groups containing oxygen only in singly bound form
C07C 67/31
By modifying the acid moiety of the ester, such modification not being an introduction of an ester group: by introduction of functional groups…
C07C
Acyclic or carbocyclic compounds

Family

US 2002/0035271 A1Pre-grant publication · published 21 Mar 2002
US 6,583,312 B2This patent

From the US filing history. Foreign family members aren’t listed.

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Abstract

A process for preparing optically active trimethyllactic acid and/or esters thereof having formula (I)

wherein R1 represents hydrogen, alkyl, aryl, aralkyl, or heterocyclyl, comprising enatiomerically hydrogenating trimethylpyruvic acid and/or esters thereof having formula (II)
wherein R1 has the meanings specified for formula (I),
in the presence of a catalyst comprising one or more noble metal complexes containing optically active bisphosphines as ligands selected from the group consisting of
(1) a bisphosphine of formula (B1)
where
R2 denotes phenyl, 3-methylphenyl, 4-methylphenyl, 3,5-dimethylphenyl, 4-methoxyphenyl, 3,5-dimethyl-4-methoxyphenyl, cyclohexyl, or cyclopentyl, or
(2) a bisphosphine of formula (B2)
where
R3 denotes phenyl, 4-methylphenyl, 3,5-dimethylphenyl, 4-methoxyphenyl, 3,5-dimethyl-4-methoxyphenyl, or cyclohexyl, or
(3) a bisphosphine of formula (B3)
where
R3 denotes phenyl, 4-methylphenyl, 3,5-dimethylphenyl, 4-methoxyphenyl, 3,5-dimethyl-4-methoxyphenyl, or cyclohexyl,
R4 denotes H, methyl, or methoxy,
R5 denotes H, methyl, methoxy, or chlorine, and
R6 denotes methyl, methoxy, or trifluoromethyl, or
(4) a bisphosphine of formula (B4)
where
R7 represents methyl, ethyl, propyl, or isopropyl, or
(5) 2,3-bis(diphenylphosphino)butane of formula (B5)
(6) 1,2-bis(diphenylphosphino)propane of formula (B6)
(7) 5,6-bis(diphenylphosphino)-2-norbornane of formula (B7)
(8) 1-substituted 3,4-bis(diphenylphosphino)pyrrolidine of formula (B8)
(9) 2,4-bis(diphenylphosphino)pentane of formula (B9)
(10) 2,3-O-isopropylidene-2,3-dihydroxy-1,4-bis(diphenylphosphino)butane of formula (B10)
(11) 1,2-bis-[(o-methoxyphenyl)phenylphosphino]ethane of formula (B11)
(12) 1-[1′,2-bis(diphenylphosphino)ferrocenyl]ethanol of formula (B12)
(13) 1-tert-butoxycarbonyl-4-diphenylphosphino-2-diphenylphosphinomethyl-pyrrolidine of formula (B13)
(14) a bisphosphine of formula (B14)
where
R8 denotes phenyl, cyclohexyl, 4-methylphenyl, 4-methoxyphenyl, 3,5-dimethylphenyl, 3,5-dimethyl-4-methoxyphenyl, 4-tert-butyl, or 3,5-di-tert-butyl, or
(15) a ferrocenyldiphosphine of formula (B15)
where
R8 denotes phenyl, cyclohexyl, 4-methylphenyl, 4-methoxyphenyl, 3,5-dimethylphenyl, 3,5-dimethyl-4-methoxyphenyl, 4-tert-butyl, or 3,5-di-tert-butyl, and
R9 denotes C1-C8-alkyl, phenyl, or phenyl monosubstituted to trisubstituted by C1-C4-alkoxy.

31 more elements

Facts

Application

09/864,906Filed 24 May 2001

Priority

DE 100 27 15431 May 2000

Published

US 2002/0035271 A121 Mar 2002

Granted

24 Jun 2003

Term ends

Not estimatedThe source records don’t support an estimate.

Classification3 codes

C07C 51/367
By reactions not involving formation of carboxyl groups: by introduction of functional groups containing oxygen only in singly bound form
C07C 67/31
By modifying the acid moiety of the ester, such modification not being an introduction of an ester group: by introduction of functional groups…
C07C
Acyclic or carbocyclic compounds