EP0918779A1 - Organoboranes chiraux - Google Patents
Organoboranes chirauxInfo
- Publication number
- EP0918779A1 EP0918779A1 EP97928339A EP97928339A EP0918779A1 EP 0918779 A1 EP0918779 A1 EP 0918779A1 EP 97928339 A EP97928339 A EP 97928339A EP 97928339 A EP97928339 A EP 97928339A EP 0918779 A1 EP0918779 A1 EP 0918779A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- compound
- formula
- general formula
- hydrogen
- compounds
- Prior art date
- 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.)
- Withdrawn
Links
- 150000001875 compounds Chemical class 0.000 claims abstract description 45
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 238000000034 method Methods 0.000 claims abstract description 8
- 125000005843 halogen group Chemical group 0.000 claims abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- 239000001257 hydrogen Substances 0.000 claims abstract description 5
- 239000003638 chemical reducing agent Substances 0.000 claims abstract description 4
- -1 cycloalkyl radical Chemical class 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 230000009467 reduction Effects 0.000 claims description 8
- 229910000039 hydrogen halide Inorganic materials 0.000 claims description 6
- 239000012433 hydrogen halide Substances 0.000 claims description 6
- 150000002576 ketones Chemical class 0.000 claims description 5
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 150000002466 imines Chemical class 0.000 claims description 3
- 125000000962 organic group Chemical group 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
- ULOIAOPTGWSNHU-UHFFFAOYSA-N 2-butyl radical Chemical compound C[CH]CC ULOIAOPTGWSNHU-UHFFFAOYSA-N 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- NQOJWOIPQBVKKX-UHFFFAOYSA-N cyclooctane Chemical compound [CH]1CCCCCCC1 NQOJWOIPQBVKKX-UHFFFAOYSA-N 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract description 5
- 229920006395 saturated elastomer Polymers 0.000 abstract description 2
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 229940125904 compound 1 Drugs 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 150000001925 cycloalkenes Chemical class 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- RRKODOZNUZCUBN-CCAGOZQPSA-N (1z,3z)-cycloocta-1,3-diene Chemical compound C1CC\C=C/C=C\C1 RRKODOZNUZCUBN-CCAGOZQPSA-N 0.000 description 2
- WQADWIOXOXRPLN-UHFFFAOYSA-N 1,3-dithiane Chemical compound C1CSCSC1 WQADWIOXOXRPLN-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 230000000707 stereoselective effect Effects 0.000 description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 2
- VYXHVRARDIDEHS-QGTKBVGQSA-N (1z,5z)-cycloocta-1,5-diene Chemical compound C\1C\C=C/CC\C=C/1 VYXHVRARDIDEHS-QGTKBVGQSA-N 0.000 description 1
- CXWGKAYMVASWDQ-UHFFFAOYSA-N 1,2-dithiane Chemical compound C1CCSSC1 CXWGKAYMVASWDQ-UHFFFAOYSA-N 0.000 description 1
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- AMKGKYQBASDDJB-UHFFFAOYSA-N 9$l^{2}-borabicyclo[3.3.1]nonane Chemical compound C1CCC2CCCC1[B]2 AMKGKYQBASDDJB-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 229910000085 borane Inorganic materials 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- LOZWAPSEEHRYPG-UHFFFAOYSA-N dithiane Natural products C1CSCCS1 LOZWAPSEEHRYPG-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000006197 hydroboration reaction Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/027—Organoboranes and organoborohydrides
Definitions
- the invention relates to chiral organoboranes, processes for their preparation and their use in particular as an asymmetric reducing agent.
- a subject of the invention is therefore compounds of general formulas I and II
- R 1 and R 2 independently represent a hydrogen atom or an alkyl or cycloalkyl radical, or R 1 and R 2 together represent a divalent saturated hydrocarbon group;
- Xl represents a halogen atom
- X2 represents a hydrogen or halogen atom
- halogen represents a fluorine, chlorine, bromine or iodine atom, preferably fluorinated, chlorine, and bromine.
- alkyl preferably represents an alkyl radical having from 1 to 6 carbon atoms, linear or branched, and in particular an alkyl radical having from 1 to 4 carbon atoms such as the methyl, ethyl, propyl, isopropyl, butyl radicals , isobutyl, sec-butyl and tert-butyl.
- the saturated cycloalkyl radicals can be chosen from radicals having from 3 to 7 carbon atoms such as the cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl radicals, optionally substituted by a lower alkyl group.
- the expression saturated divalent hydrocarbon group comprises from 6 to 8 carbon atoms and can be represented by a bicyclo group [5,1,1], [4,1,2], [3,1,3], [ 4.1.1], [3.1.2], [3.1.1] or [2.1.2], and preferably of the type [3.1.3].
- a subject of the invention is also a process for preparing the compounds of general formula I as defined above, characterized in that a compound of general formula III is reacted
- suitable unsaturated hydrogenated compound represents a hydrocarbon compound comprising one or two double bond (s).
- organic group represents an alkyl or aryl radical, and preferably an alkyl radical such as tert-butyl.
- a cycloalkyldiene comprising from 6 to 8 carbon atoms
- R] and R2 together represent a divalent saturated hydrocarbon group of 6 to 8 atoms respectively.
- the production of an alkyl and / or cycloalkyl radical on the boron atom of the compound of formula I is obtained by reacting the corresponding alkene and / or cycloalkene (s) respectively, with the compound of formula III.
- the invention also relates to a process for the preparation of the compounds of general formula II as defined above.
- the process for the preparation of a compound of formula II in which X ⁇ has the meaning indicated above and X 2 represents hydrogen is characterized in that a compound of general formula III as defined below is reacted above, with one mole of a hydrogen halide of formula HXi, in which Xj has the meaning indicated above.
- the process for the preparation of a compound of formula II in which Xi has the meaning indicated above and X 2 represents a halogen is characterized in that a compound of general formula III as defined above is reacted , with one mole of a hydrogen halide HXi and one mole of the hydrogen halide HX2.
- X] and X2 can represent the same halogen atom.
- the starting compound IH is known; it can be prepared by hydroboration of 2-myrtényl 1,3-dithiane with diborane or by a complex of diborane with a Lewis acid (patent EP 61408).
- the compounds of formula I and II can thus be prepared in optically active form, from compound IH in optically active form.
- the compounds of the present invention are useful as an asymmetric reducing agent.
- a subject of the invention is therefore also the use of the compounds of formula I and II for asymmetric reductions.
- the compounds of the present invention are used for the stereospecific reduction of ketone or imine function (s).
- the stereospecific reduction of ketone or imine consists in reacting the ketone or rimine with an enantiomer of a compound of general formula I or H.
- the white solid is collected in 20 ml of anhydrous tetrahydrofuran and used as such in the reductions.
- the compound (+) 2 is crystallized from hexane (530 ml), to give 52.1 g with a composition 98.2% (-) / 1.8% ( +).
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9607331A FR2749847B1 (fr) | 1996-06-13 | 1996-06-13 | Organoboranes chiraux |
| FR9607331 | 1996-06-13 | ||
| PCT/FR1997/001050 WO1997047628A1 (fr) | 1996-06-13 | 1997-06-12 | Organoboranes chiraux |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP0918779A1 true EP0918779A1 (fr) | 1999-06-02 |
Family
ID=9493012
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP97928339A Withdrawn EP0918779A1 (fr) | 1996-06-13 | 1997-06-12 | Organoboranes chiraux |
Country Status (8)
| Country | Link |
|---|---|
| EP (1) | EP0918779A1 (no) |
| JP (1) | JP2000511922A (no) |
| AU (1) | AU714166B2 (no) |
| CA (1) | CA2257678A1 (no) |
| FR (1) | FR2749847B1 (no) |
| NO (1) | NO985832L (no) |
| NZ (1) | NZ333451A (no) |
| WO (1) | WO1997047628A1 (no) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4536931B2 (ja) * | 1999-01-19 | 2010-09-01 | ビーエーエスエフ ソシエタス・ヨーロピア | 置換ホウ水素化アルカリ金属反応体の合成法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA821644B (en) * | 1981-03-25 | 1983-01-26 | Expansia Sa | Borane complexes |
-
1996
- 1996-06-13 FR FR9607331A patent/FR2749847B1/fr not_active Expired - Fee Related
-
1997
- 1997-06-12 EP EP97928339A patent/EP0918779A1/fr not_active Withdrawn
- 1997-06-12 AU AU32669/97A patent/AU714166B2/en not_active Ceased
- 1997-06-12 WO PCT/FR1997/001050 patent/WO1997047628A1/fr not_active Application Discontinuation
- 1997-06-12 NZ NZ333451A patent/NZ333451A/xx unknown
- 1997-06-12 CA CA 2257678 patent/CA2257678A1/fr not_active Abandoned
- 1997-06-12 JP JP10501309A patent/JP2000511922A/ja active Pending
-
1998
- 1998-12-11 NO NO985832A patent/NO985832L/no not_active Application Discontinuation
Non-Patent Citations (1)
| Title |
|---|
| See references of WO9747628A1 * |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2000511922A (ja) | 2000-09-12 |
| NZ333451A (en) | 1999-08-30 |
| NO985832D0 (no) | 1998-12-11 |
| NO985832L (no) | 1998-12-14 |
| FR2749847B1 (fr) | 1998-11-06 |
| FR2749847A1 (fr) | 1997-12-19 |
| WO1997047628A1 (fr) | 1997-12-18 |
| AU3266997A (en) | 1998-01-07 |
| CA2257678A1 (fr) | 1997-12-18 |
| AU714166B2 (en) | 1999-12-23 |
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