CA1100512A - Obtention d'iodures de certains complexes de rhodium et de certaines diphosphines asymetriques servant a accroitre l'enantioselectivite des produits de leur reduction d'imidazolines prochirales - Google Patents

Obtention d'iodures de certains complexes de rhodium et de certaines diphosphines asymetriques servant a accroitre l'enantioselectivite des produits de leur reduction d'imidazolines prochirales

Info

Publication number: CA1100512A
Authority: CA; Canada
Prior art keywords: complex; reduction; enantioselectivity; asymmetric; cod
Prior art date: 1977-06-14
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.): Expired

Application number

CA303,716A

Other languages

English (en)

Inventor

Robert G. Fischer, Jr.

Arnold Zweig

Sivaraman Raghu

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Wyeth Holdings LLC

Original Assignee

American Cyanamid Co

Priority date (The priority date 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 date listed.)

1977-06-14

Filing date

1978-05-19

Publication date

1981-05-05

1978-05-19 Application filed by American Cyanamid Co filed Critical American Cyanamid Co

1981-05-05 Application granted granted Critical

1981-05-05 Publication of CA1100512A publication Critical patent/CA1100512A/fr

Status Expired legal-status Critical Current

Links

238000002360 preparation method Methods 0.000 title claims description 3
230000009467 reduction Effects 0.000 title abstract description 23
150000004694 iodide salts Chemical class 0.000 title abstract description 5
150000003283 rhodium Chemical class 0.000 title description 5
CAAMSDWKXXPUJR-UHFFFAOYSA-N 3,5-dihydro-4H-imidazol-4-one Chemical class O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 title 1
238000000034 method Methods 0.000 claims abstract description 21
239000003054 catalyst Substances 0.000 claims description 21
XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 15
XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 claims description 11
229910000073 phosphorus hydride Inorganic materials 0.000 claims description 7
239000002904 solvent Substances 0.000 claims description 6
XLYDVEDKLHRLLS-UHFFFAOYSA-N phenyl-[[2-(phenylphosphanylmethyl)cyclobutyl]methyl]phosphane Chemical compound C1CC(CPC=2C=CC=CC=2)C1CPC1=CC=CC=C1 XLYDVEDKLHRLLS-UHFFFAOYSA-N 0.000 claims description 4
150000001875 compounds Chemical class 0.000 claims description 3
230000006872 improvement Effects 0.000 claims description 3
125000002252 acyl group Chemical group 0.000 claims description 2
HLFSDGLLUJUHTE-SNVBAGLBSA-N Levamisole Chemical compound C1([C@H]2CN3CCSC3=N2)=CC=CC=C1 HLFSDGLLUJUHTE-SNVBAGLBSA-N 0.000 abstract description 8
229960001614 levamisole Drugs 0.000 abstract description 8
-1 (-) Chemical compound 0.000 abstract description 5
238000004519 manufacturing process Methods 0.000 abstract description 2
150000003003 phosphines Chemical group 0.000 abstract description 2
HLFSDGLLUJUHTE-UHFFFAOYSA-N 6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b][1,3]thiazole Chemical compound N1=C2SCCN2CC1C1=CC=CC=C1 HLFSDGLLUJUHTE-UHFFFAOYSA-N 0.000 abstract 1
230000000507 anthelmentic effect Effects 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
239000010948 rhodium Substances 0.000 description 39
238000006722 reduction reaction Methods 0.000 description 21
239000000463 material Substances 0.000 description 15
239000000047 product Substances 0.000 description 13
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 11
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
238000005984 hydrogenation reaction Methods 0.000 description 9
229910052703 rhodium Inorganic materials 0.000 description 8
JJWACYUTERPMBM-UHFFFAOYSA-N 1-acetylimidazolidin-2-one Chemical compound CC(=O)N1CCNC1=O JJWACYUTERPMBM-UHFFFAOYSA-N 0.000 description 7
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
238000006243 chemical reaction Methods 0.000 description 7
239000000243 solution Substances 0.000 description 7
239000000758 substrate Substances 0.000 description 7
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
239000000203 mixture Substances 0.000 description 6
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 description 5
229960001701 chloroform Drugs 0.000 description 5
YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
238000005481 NMR spectroscopy Methods 0.000 description 4
VURFVHCLMJOLKN-UHFFFAOYSA-N diphosphane Chemical compound PP VURFVHCLMJOLKN-UHFFFAOYSA-N 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
150000001450 anions Chemical class 0.000 description 3
238000006555 catalytic reaction Methods 0.000 description 3
238000010531 catalytic reduction reaction Methods 0.000 description 3
239000003446 ligand Substances 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
239000012044 organic layer Substances 0.000 description 3
230000008569 process Effects 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
239000004912 1,5-cyclooctadiene Substances 0.000 description 2
ASUDFOJKTJLAIK-UHFFFAOYSA-N 2-methoxyethanamine Chemical compound COCCN ASUDFOJKTJLAIK-UHFFFAOYSA-N 0.000 description 2
BVHHMHMXFWJGOF-UHFFFAOYSA-N 3-acetyl-1-(2-methoxyethyl)-4-phenylimidazolidin-2-one Chemical compound CC(=O)N1C(=O)N(CCOC)CC1C1=CC=CC=C1 BVHHMHMXFWJGOF-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
229960000583 acetic acid Drugs 0.000 description 2
150000001336 alkenes Chemical class 0.000 description 2
150000001371 alpha-amino acids Chemical class 0.000 description 2
235000008206 alpha-amino acids Nutrition 0.000 description 2
230000003197 catalytic effect Effects 0.000 description 2
150000003841 chloride salts Chemical class 0.000 description 2
239000013078 crystal Substances 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 2
YXJPWWGLCOPUGI-NCJHBDPTSA-N europium;(2z)-4,7,7-trimethyl-2-(2,2,2-trifluoro-1-hydroxyethylidene)bicyclo[2.2.1]heptan-3-one Chemical compound [Eu].C1CC2(C)C(=O)\C(=C(/O)C(F)(F)F)C1C2(C)C.C1CC2(C)C(=O)\C(=C(/O)C(F)(F)F)C1C2(C)C.C1CC2(C)C(=O)\C(=C(/O)C(F)(F)F)C1C2(C)C YXJPWWGLCOPUGI-NCJHBDPTSA-N 0.000 description 2
238000001914 filtration Methods 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
239000010410 layer Substances 0.000 description 2
FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 2
239000002243 precursor Substances 0.000 description 2
239000003579 shift reagent Substances 0.000 description 2
235000009518 sodium iodide Nutrition 0.000 description 2
239000007787 solid Substances 0.000 description 2
238000001665 trituration Methods 0.000 description 2
238000010626 work up procedure Methods 0.000 description 2
AICIYIDUYNFPRY-UHFFFAOYSA-N 1,3-dihydro-2H-imidazol-2-one Chemical class O=C1NC=CN1 AICIYIDUYNFPRY-UHFFFAOYSA-N 0.000 description 1
VYXHVRARDIDEHS-UHFFFAOYSA-N 1,5-cyclooctadiene Chemical compound C1CC=CCCC=C1 VYXHVRARDIDEHS-UHFFFAOYSA-N 0.000 description 1
LSPYWVHGMGMIPG-UHFFFAOYSA-N 1-(2-methoxybenzoyl)imidazolidin-2-one Chemical compound COC1=CC=CC=C1C(=O)N1C(=O)NCC1 LSPYWVHGMGMIPG-UHFFFAOYSA-N 0.000 description 1
VXGIVSQSOWUZJO-UHFFFAOYSA-N 1-(cyclohexanecarbonyl)imidazolidin-2-one Chemical compound C1CNC(=O)N1C(=O)C1CCCCC1 VXGIVSQSOWUZJO-UHFFFAOYSA-N 0.000 description 1
AJSFBSYWKIBTGP-UHFFFAOYSA-N 1-benzoylimidazolidin-2-one Chemical compound C=1C=CC=CC=1C(=O)N1CCNC1=O AJSFBSYWKIBTGP-UHFFFAOYSA-N 0.000 description 1
LKQSEFCGKYFESN-UHFFFAOYSA-N 2-(2-methylphenoxy)-4h-1,3,2$l^{5}-benzodioxaphosphinine 2-oxide Chemical compound CC1=CC=CC=C1OP1(=O)OC2=CC=CC=C2CO1 LKQSEFCGKYFESN-UHFFFAOYSA-N 0.000 description 1
VYTGHVXARUHBJL-UHFFFAOYSA-N 2-bromo-1-phenylethanone 3-(2-methoxyethyl)-5-phenyl-1H-imidazol-2-one Chemical compound C(C(=O)C1=CC=CC=C1)Br.COCCN1C(NC(=C1)C1=CC=CC=C1)=O VYTGHVXARUHBJL-UHFFFAOYSA-N 0.000 description 1
XHIUFYZDQBSEMF-UHFFFAOYSA-N 2-methylbutyl acetate Chemical compound CCC(C)COC(C)=O XHIUFYZDQBSEMF-UHFFFAOYSA-N 0.000 description 1
UXERCGOLBABXTB-UHFFFAOYSA-N 3-(2-methoxyethyl)-5-phenyl-1h-imidazol-2-one Chemical compound N1C(=O)N(CCOC)C=C1C1=CC=CC=C1 UXERCGOLBABXTB-UHFFFAOYSA-N 0.000 description 1
WUUSKKYXRAMVAT-UHFFFAOYSA-N 3-(cyclohexanecarbonyl)-1-(2-methoxyethyl)-4-phenylimidazolidin-2-one Chemical compound O=C1N(CCOC)CC(C=2C=CC=CC=2)N1C(=O)C1CCCCC1 WUUSKKYXRAMVAT-UHFFFAOYSA-N 0.000 description 1
DYXLJVBGQMMTHR-UHFFFAOYSA-N 3-acetyl-1-(2-methoxyethyl)-4-phenylimidazol-2-one Chemical compound CC(=O)N1C(=O)N(CCOC)C=C1C1=CC=CC=C1 DYXLJVBGQMMTHR-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
229910052693 Europium Inorganic materials 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-XIXRPRMCSA-N Mesotartaric acid Chemical compound OC(=O)[C@@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-XIXRPRMCSA-N 0.000 description 1
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
241000206607 Porphyra umbilicalis Species 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
208000036366 Sensation of pressure Diseases 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
230000009471 action Effects 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
235000001014 amino acid Nutrition 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
238000009876 asymmetric hydrogenation reaction Methods 0.000 description 1
238000011914 asymmetric synthesis Methods 0.000 description 1
AMZTWVMARTWHPA-UVMMSNCQSA-N butyl (2s,4s)-4-diphenylphosphanyl-2-(diphenylphosphanylmethyl)pyrrolidine-1-carboxylate Chemical compound C([C@@H]1C[C@@H](CN1C(=O)OCCCC)P(C=1C=CC=CC=1)C=1C=CC=CC=1)P(C=1C=CC=CC=1)C1=CC=CC=C1 AMZTWVMARTWHPA-UVMMSNCQSA-N 0.000 description 1
AMZTWVMARTWHPA-UHFFFAOYSA-N butyl 4-diphenylphosphanyl-2-(diphenylphosphanylmethyl)pyrrolidine-1-carboxylate Chemical compound CCCCOC(=O)N1CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1CP(C=1C=CC=CC=1)C1=CC=CC=C1 AMZTWVMARTWHPA-UHFFFAOYSA-N 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
229960004132 diethyl ether Drugs 0.000 description 1
230000000694 effects Effects 0.000 description 1
125000005610 enamide group Chemical group 0.000 description 1
239000011982 enantioselective catalyst Substances 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
239000002815 homogeneous catalyst Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
238000006459 hydrosilylation reaction Methods 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
XULSCZPZVQIMFM-IPZQJPLYSA-N odevixibat Chemical compound C12=CC(SC)=C(OCC(=O)N[C@@H](C(=O)N[C@@H](CC)C(O)=O)C=3C=CC(O)=CC=3)C=C2S(=O)(=O)NC(CCCC)(CCCC)CN1C1=CC=CC=C1 XULSCZPZVQIMFM-IPZQJPLYSA-N 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
LIGACIXOYTUXAW-UHFFFAOYSA-N phenacyl bromide Chemical compound BrCC(=O)C1=CC=CC=C1 LIGACIXOYTUXAW-UHFFFAOYSA-N 0.000 description 1
CHOLPKIHPFNIPE-UHFFFAOYSA-N phosphanylphosphane rhodium Chemical compound [Rh].PP CHOLPKIHPFNIPE-UHFFFAOYSA-N 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
WMOVHXAZOJBABW-UHFFFAOYSA-N tert-butyl acetate Chemical compound CC(=O)OC(C)(C)C WMOVHXAZOJBABW-UHFFFAOYSA-N 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Catalysts (AREA)

CA303,716A 1977-06-14 1978-05-19 Obtention d'iodures de certains complexes de rhodium et de certaines diphosphines asymetriques servant a accroitre l'enantioselectivite des produits de leur reduction d'imidazolines prochirales Expired CA1100512A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US80642177A	1977-06-14	1977-06-14
US806,421		1977-06-14

Publications (1)

Publication Number	Publication Date
CA1100512A true CA1100512A (fr)	1981-05-05

Family

ID=25194010

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA303,716A Expired CA1100512A (fr)	1977-06-14	1978-05-19	Obtention d'iodures de certains complexes de rhodium et de certaines diphosphines asymetriques servant a accroitre l'enantioselectivite des produits de leur reduction d'imidazolines prochirales

Country Status (1)

Country	Link
CA (1)	CA1100512A (fr)

1978
- 1978-05-19 CA CA303,716A patent/CA1100512A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1998-05-05	MKEX	Expiry

Publication	Publication Date	Title
US4010181A (en)	1977-03-01	Process for the asymmetric hydrogenation of a substituted acrylic acid or ester thereof
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DE3874619T2 (de)	1993-04-15	Herstellungsverfahren eines optisch aktiven alkohols.
US6525210B1 (en)	2003-02-25	Chiral ligands, transition-metal complexes thereof and uses thereof in asymmetric reactions
US4851537A (en)	1989-07-25	Process for preparing N-acyltetrahydroisoquinoline
US6037505A (en)	2000-03-14	Enantioselective oxazaborolidine catalysts
EP0582668B1 (fr)	1997-11-19	Ligands de bis(phospholanes) tridentes chiraux
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EP0452143A2 (fr)	1991-10-16	Procédé pour la préparation de dérivés optiquement actifs de 3-hydroxypyrrolidine
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CA2671830A1 (fr)	2008-06-19	Procede catalytique pour hydrogenation asymetrique
CA1142947A (fr)	1983-03-15	Composes 1,2-bis-(diphenyl-phosphino) optiquement actifs; complexes metalliques qui en renferment sous forme de ligandes chiraux, et applications
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US4168381A (en)	1979-09-18	Enhancement of enantioselectivity by iodide salts of Rh(I) complexes in the reduction of prochiral imidazolinones
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US5258553A (en)	1993-11-02	Chiral tridentate bis(phospholane) ligands
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