Title of Invention	"A PROCESS FOR THE PREPATATION OF OPTICALLY ACTIVE SUBSTITUTED ALPHA-AMINO-INDANE DERIVATIVES"
Abstract	"NEW PROCESS FOR THE SYNTHESIS OF SUBSTITUTED ALPHA AMINOINDAN DERIVATIVES" A process for the preparation of optically active substituted alpha-indanyl amide derivatives of formula (1), which comprise*: - an asymmetric hydrogenation reaction of an en-amide derivative of formula (III) in presence of hydrogen and an optically active catalyst, in order to obtain an amide derivative of formula (II), a hydrolysis reaction of the amide derivative of formula (II) obtained in the previous step, in order to obtain optically active substituted alphaindanyl amide derivatives of formula (I). Formula (1), Formula (I!) and Formula (III),

Title of Invention

"A PROCESS FOR THE PREPATATION OF OPTICALLY ACTIVE SUBSTITUTED ALPHA-AMINO-INDANE DERIVATIVES"

Abstract

"NEW PROCESS FOR THE SYNTHESIS OF SUBSTITUTED ALPHA AMINOINDAN DERIVATIVES" A process for the preparation of optically active substituted alpha-indanyl amide derivatives of formula (1), which comprise*: - an asymmetric hydrogenation reaction of an en-amide derivative of formula (III) in presence of hydrogen and an optically active catalyst, in order to obtain an amide derivative of formula (II), a hydrolysis reaction of the amide derivative of formula (II) obtained in the previous step, in order to obtain optically active substituted alphaindanyl amide derivatives of formula (I). Formula (1), Formula (I!) and Formula (III),

Full Text	We Claim: 1. A process for the preparation of optically active substituted alpha-amino-indane derivatives of formula (I): (Formula Removed) wherein m is an integer equal to 0, 1, 2 or 3, R1 is a hydrogen atom, an alkyl group having from 1 to 20 carbon atoms, an aryl group having from 6 to 20 carbon atoms, an alkylaryl group having from 6 to 20 carbon atoms, an alkaloyl group, an aryloyl group, which comprises the steps of: (i)an asymmetric hydrogenation reaction of an en-amide derivative of formula (III) (Formula Removed) wherein m and R1 are as defined above, R2 is a hydrogen atom, an alkyl group having from 1 to 20 carbon atoms, an aryl group having from 6 to 20 carbon atoms, an alkylaryl group having from 6 to 20 carbon atoms, in the presence of hydrogen, an optically active catalyst and a solvent, to obtain an amide derivative of formula (II) : (Formula Removed) (ii)a hydrolysis reaction of the amide derivative of formula (II) obtained in the previous step, to obtain optically active substituted alpha-amino-indane derivatives of formula (I) wherein the optically active catalyst used in the asymmetric hydrogenation of the en-amide derivative of formula (III) is represented by a chiral phosphine transition metal complex of formula (VIIA) (Formula Removed) Wherein M is ruthenium (Ru), X is a halogen atom selected in the group comprising chlorine (C1), bromine (Br), fluorine (F) and iodine (I), Z is an aryl group having from 6 to 20 carbon atoms or an unsaturated organic group, cyclic or not, selected in the group comprising define, diene and cyano, L* is a chiral ligand selected in the group comprising the chiral diphosphine derivatives, the chiral atropoisomeric diphosphine derivatives, the chiral monodentate phosphoramidine derivatives, the chiral biphospholane derivatives, the chiral ferrotane derivatives and the chiral ferrocenyl phosphine derivatives, Y is an anion such as C104-, BF4-, PF6-, SbF6-, j is an integer equal to 0 or 1, i is an integer equal to 0, 1, 2 or 4, n is an integer equal to 1 or 2; wherein the molar ratio of the en-amide derivative of formula (III) to the catalyst (VII) used during the asymmetric hydrogenation is from 100/1 to 10000/1; Wherein the hydrogen pressure used during the asymmetric hydrogenation is from 0.5 to 20 bars; and Wherein the temperature range used during the asymmetric hydrogenation is from - 20°C to 100°c. 2. The process as claimed in claim 1, wherein the oefine is selected in the group comprising pi-allyl and 1, 3, 5, 7-cyclooctatetraene and the diene is selected in the group comprising 1, 3-butadiene, 2,5-norbornadiene, 1, 5-cyclooctadiene (COD) and cyclopentadiene. 3. The process as claimed in claim 1, wherein the aryl group is a benzene optionally substituted with an alkyl. 4. The process as claimed in claim 1, wherein the chiral diphosphine is selected in the group comprising BICP, DuPHOS, MiniPHOS, BDPMI, TangPHOS, P-PHOS, Tol-P-PHOS, Xyl-P-PHOS and BPE. . 5. The process as claimed in claim 1, wherein the chiral atropoisomeric diphosphine is selected in the group comprising BINAP, TolBINAP, MeOBIPHEP, BINAPO, SYNPHOS and BINAPO optionally ortho-substituted with an alkyl or an aryl. 6. The process as claimed in claim 1, wherein the chiral monodentate phosphoramidine is selected in the group comprising Monophos and Ethylmonophos. 7. The process as claimed in claim 1, wherein the chiral bisphospholane is selected in the group comprising Tangphos, Duphos, Me-Duphos Me-BPE, Et-BPE, Binaphane and Malphos. 8. The process as claimed in claim 1, wherein the chiral ferrocenyl phosphine is JOSIPHOS. 9. The process as claimed in any one of claims 1 to 8, wherein the optically active catalyst is Ru (COD) (MeOBIPHEP) BF4- or Ru (COD) (BINAP) BF4-. 10. The process as claimed in any one of claims 1 to 9, wherein the solvent used during the asymmetric hydrogenation is selected in the group comprising ether, aromatic hydrocarbon halogenated hydrocarbon and alcohol, preferably an alcohol. 11. The process as claimed claim 10, wherein the ether is selected in the group comprising tetrahydrofuran (THF), tetrahydropyran and diethyl ether, the aromatic hydrocarbon is selected in the group comprising benzene and toluene, the halogenated hydrocarbon is dichloromethane, the alcohol is selected in the group comprising methanol, ethanol and isopropanol, and is preferably the methanol. 12. The process as claimed in any one of claims 1 to 11, wherein the molar ratio of the en-amide derivative of formula (III) to the catalyst (VII) used during the asymmetric hydrogenation is from 100/1 to 1000/1 and more preferably from 200/1 to 1000/1. 13. The process as claimed in any one of claims 1 to 12, wherein the hydrogen pressure used during the asymmetric hydrogenation is from 1 to 8 bars. 14 . The process as claimed in any one of claims 1 to 13, wherein the temperature range used during the asymmetric hydrogenation is from 20 to 100°C, preferably from 20°C to 60°C.

Full Text

We Claim:
1. A process for the preparation of optically active substituted alpha-amino-indane derivatives of formula (I):
(Formula Removed)
wherein
m is an integer equal to 0, 1, 2 or 3,
R1 is a hydrogen atom, an alkyl group having from 1 to 20 carbon atoms, an aryl group having from 6 to 20 carbon atoms, an alkylaryl group having from 6 to 20 carbon atoms, an alkaloyl group, an aryloyl group,
which comprises the steps of:
(i)an asymmetric hydrogenation reaction of an en-amide derivative of formula (III)
(Formula Removed)
wherein m and R1 are as defined above,
R2 is a hydrogen atom, an alkyl group having from 1 to 20 carbon atoms, an aryl group having from 6 to 20 carbon atoms, an alkylaryl group having from 6 to 20 carbon atoms,
in the presence of hydrogen, an optically active catalyst and a solvent,
to obtain an amide derivative of formula (II) :
(Formula Removed)
(ii)a hydrolysis reaction of the amide derivative of formula (II) obtained in the previous step,
to obtain optically active substituted alpha-amino-indane derivatives of formula (I) wherein the optically active catalyst used in the asymmetric hydrogenation of the en-amide derivative of formula (III) is represented by a chiral phosphine transition metal complex of formula (VIIA)
(Formula Removed)
Wherein
M is ruthenium (Ru),
X is a halogen atom selected in the group comprising chlorine (C1), bromine (Br), fluorine (F) and iodine (I),
Z is an aryl group having from 6 to 20 carbon atoms or an unsaturated organic group, cyclic or not, selected in the group comprising define, diene and cyano,
L* is a chiral ligand selected in the group comprising the chiral diphosphine derivatives, the chiral atropoisomeric diphosphine derivatives, the chiral monodentate phosphoramidine derivatives, the chiral biphospholane derivatives, the chiral ferrotane derivatives and the chiral ferrocenyl phosphine derivatives,
Y is an anion such as C104-, BF4-, PF6-, SbF6-,
j is an integer equal to 0 or 1,
i is an integer equal to 0, 1, 2 or 4,
n is an integer equal to 1 or 2; wherein the molar ratio of the en-amide derivative of formula (III) to the catalyst (VII) used during the asymmetric hydrogenation is from 100/1 to 10000/1; Wherein the hydrogen pressure used during the asymmetric hydrogenation is from 0.5 to 20 bars; and
Wherein the temperature range used during the asymmetric hydrogenation is from - 20°C to 100°c.
2. The process as claimed in claim 1, wherein the oefine is selected in the group comprising pi-allyl and 1, 3, 5, 7-cyclooctatetraene and the diene is selected in the group comprising 1, 3-butadiene, 2,5-norbornadiene, 1, 5-cyclooctadiene (COD) and cyclopentadiene.
3. The process as claimed in claim 1, wherein the aryl group is a benzene optionally substituted with an alkyl.
4. The process as claimed in claim 1, wherein the chiral diphosphine is selected in the group comprising BICP, DuPHOS, MiniPHOS, BDPMI, TangPHOS, P-PHOS, Tol-P-PHOS, Xyl-P-PHOS and BPE.
. 5. The process as claimed in claim 1, wherein the chiral atropoisomeric diphosphine is selected in the group comprising BINAP, TolBINAP, MeOBIPHEP, BINAPO, SYNPHOS and
BINAPO optionally ortho-substituted with an alkyl or an aryl.
6. The process as claimed in claim 1, wherein the chiral monodentate phosphoramidine is selected in the group comprising Monophos and Ethylmonophos.
7. The process as claimed in claim 1, wherein the chiral bisphospholane is selected in the group comprising Tangphos, Duphos, Me-Duphos Me-BPE, Et-BPE, Binaphane and Malphos.
8. The process as claimed in claim 1, wherein the chiral ferrocenyl phosphine is JOSIPHOS.
9. The process as claimed in any one of claims 1 to
8, wherein the optically active catalyst is Ru (COD)
(MeOBIPHEP) BF4- or Ru (COD) (BINAP) BF4-.
10. The process as claimed in any one of claims 1 to
9, wherein the solvent used during the asymmetric
hydrogenation is selected in the group comprising ether,
aromatic hydrocarbon halogenated hydrocarbon and alcohol,
preferably an alcohol.
11. The process as claimed claim 10, wherein the ether
is selected in the group comprising tetrahydrofuran (THF),
tetrahydropyran and diethyl ether, the aromatic hydrocarbon
is selected in the group comprising benzene and toluene,
the halogenated hydrocarbon is dichloromethane, the alcohol
is selected in the group comprising methanol, ethanol and
isopropanol, and is preferably the methanol.
12. The process as claimed in any one of claims 1 to
11, wherein the molar ratio of the en-amide derivative of
formula (III) to the catalyst (VII) used during the
asymmetric hydrogenation is from 100/1 to 1000/1 and more
preferably from 200/1 to 1000/1.
13. The process as claimed in any one of claims 1 to
12, wherein the hydrogen pressure used during the
asymmetric hydrogenation is from 1 to 8 bars.
14 . The process as claimed in any one of claims 1 to
13, wherein the temperature range used during the asymmetric hydrogenation is from 20 to 100°C, preferably from 20°C to 60°C.

Documents:

4627-delnp-2006-abstract.pdf

4627-DELNP-2006-Claims-(04-07-2011).pdf

4627-DELNP-2006-Claims-(28-03-2012).pdf

4627-delnp-2006-claims.pdf

4627-DELNP-2006-Correspondence Others-(04-07-2011).pdf

4627-DELNP-2006-Correspondence Others-(28-03-2012).pdf

4627-delnp-2006-Correspondence-Others-(16-10-2007).pdf

4627-delnp-2006-correspondence-others.pdf

4627-DELNP-2006-Drawings-(28-03-2012).pdf

4627-delnp-2006-drawings.pdf

4627-DELNP-2006-Form-1-(04-07-2011).pdf

4627-delnp-2006-form-1.pdf

4627-delnp-2006-form-13.pdf

4627-delnp-2006-Form-18-(16-10-2007).pdf

4627-DELNP-2006-Form-2-(04-07-2011).pdf

4627-delnp-2006-form-2.pdf

4627-delnp-2006-form-26.pdf

4627-DELNP-2006-Form-3-(04-07-2011).pdf

4627-delnp-2006-form-3.pdf

4627-delnp-2006-form-5.pdf

4627-DELNP-2006-GPA-(04-07-2011).pdf

4627-delnp-2006-pct-210.pdf

4627-delnp-2006-pct-220.pdf

4627-delnp-2006-pct-237.pdf

4627-delnp-2006-pct-301.pdf

4627-delnp-2006-pct-304.pdf

4627-delnp-2006-pct-308.pdf

4627-DELNP-2006-Petition-137-(04-07-2011).pdf

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Patent Number

252256

Indian Patent Application Number

4627/DELNP/2006

PG Journal Number

19/2012

Publication Date

11-May-2012

Grant Date

03-May-2012

Date of Filing

10-Aug-2006

Name of Patentee

PPG-SIPSY

Applicant Address

73 RUE DU DOCTEUR CHAILOUX-49330 CHAMPIGNE- FRANCE

Inventors:

#	Inventor's Name	Inventor's Address
1	BERTRAND, BLANDINE	BASCLOT, F-49440, ANGRIE, FRANCE.
2	BLANCHET, SYLVIE	LOTISSEMENT DU PETIT, F-49460 FENEU, FRANCE
3	BURGOS, ALAIN	9, RUE PAUL GAUGUIN, F-49130 LES POINTS-DE-CE, FRANCE
4	ROUSSIASSE, SONIA	73 RUE DU DOCTEUR CHAILLOUX-49330 CHAMPIGNE-FRANCE
5	DERRIEN, YVON	12, RUE DES MOISSONS, F-49770 LA MEIGNANNE, FRANCE
6	MARTIN, JULIETTE	2 RESIDENCE MONTESQUIEU, F-49100 ANGERS, FRANCE
7	PERRIN, FLORENCE	12, ALLEE GARCIA LORCA, F-49240 AVRILLE, FRANCE

PCT International Classification Number

C07C 213/02

PCT International Application Number

PCT/IB2005/000534

PCT International Filing date

2005-02-21

PCT Conventions:

#	PCT Application Number	Date of Convention	Priority Country
1	04290444.1	2004-02-19	EUROPEAN UNION