JP5330706B2 - 光学活性3−キヌクリジノールの製造方法 - Google Patents
光学活性3−キヌクリジノールの製造方法 Download PDFInfo
- Publication number
- JP5330706B2 JP5330706B2 JP2008035673A JP2008035673A JP5330706B2 JP 5330706 B2 JP5330706 B2 JP 5330706B2 JP 2008035673 A JP2008035673 A JP 2008035673A JP 2008035673 A JP2008035673 A JP 2008035673A JP 5330706 B2 JP5330706 B2 JP 5330706B2
- Authority
- JP
- Japan
- Prior art keywords
- optically active
- group
- quinuclidinol
- substituent
- diamine
- 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.)
- Expired - Fee Related
Links
- IVLICPVPXWEGCA-UHFFFAOYSA-N 3-quinuclidinol Chemical compound C1C[C@@H]2C(O)C[N@]1CC2 IVLICPVPXWEGCA-UHFFFAOYSA-N 0.000 title claims description 35
- 238000000034 method Methods 0.000 title claims description 8
- 150000004985 diamines Chemical class 0.000 claims description 25
- ZKMZPXWMMSBLNO-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octan-3-one Chemical compound C1CC2C(=O)CN1CC2 ZKMZPXWMMSBLNO-UHFFFAOYSA-N 0.000 claims description 24
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 18
- 125000001424 substituent group Chemical group 0.000 claims description 18
- 238000004519 manufacturing process Methods 0.000 claims description 12
- 239000012327 Ruthenium complex Substances 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 125000002723 alicyclic group Chemical group 0.000 claims description 6
- 238000005984 hydrogenation reaction Methods 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 description 29
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- -1 ruthenium diamine Chemical class 0.000 description 20
- 229910052757 nitrogen Inorganic materials 0.000 description 14
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
- 239000002585 base Substances 0.000 description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 229910052707 ruthenium Inorganic materials 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- SSJXIUAHEKJCMH-WDSKDSINSA-N (1s,2s)-cyclohexane-1,2-diamine Chemical compound N[C@H]1CCCC[C@@H]1N SSJXIUAHEKJCMH-WDSKDSINSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- VURFVHCLMJOLKN-UHFFFAOYSA-N diphosphane Chemical compound PP VURFVHCLMJOLKN-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- 150000001728 carbonyl compounds Chemical class 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000003446 ligand Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- DGIPOKRRLDGGEE-QZTJIDSGSA-N (1R,2R)-1,2-bis(4-methoxyphenyl)-N,N'-dimethylethane-1,2-diamine Chemical compound C1([C@@H](NC)[C@H](NC)C=2C=CC(OC)=CC=2)=CC=C(OC)C=C1 DGIPOKRRLDGGEE-QZTJIDSGSA-N 0.000 description 2
- RXHWPJDPYDGJNR-ROUUACIJSA-N (1S,2S)-N,N'-dimethyl-1,2-bis(2-methylphenyl)ethane-1,2-diamine Chemical compound CC1=CC=CC=C1[C@@H]([C@H](C2=CC=CC=C2C)NC)NC RXHWPJDPYDGJNR-ROUUACIJSA-N 0.000 description 2
- JRHPOFJADXHYBR-HTQZYQBOSA-N (1r,2r)-1-n,2-n-dimethylcyclohexane-1,2-diamine Chemical compound CN[C@@H]1CCCC[C@H]1NC JRHPOFJADXHYBR-HTQZYQBOSA-N 0.000 description 2
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical group [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 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 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 2
- 229910052703 rhodium Inorganic materials 0.000 description 2
- 239000010948 rhodium Substances 0.000 description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 2
- YAYGSLOSTXKUBW-UHFFFAOYSA-N ruthenium(2+) Chemical compound [Ru+2] YAYGSLOSTXKUBW-UHFFFAOYSA-N 0.000 description 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 2
- DMKKIUIRZXFPDW-CLJLJLNGSA-N (1R,2R)-N,N'-dicyclohexyl-1,2-diphenylethane-1,2-diamine Chemical compound C1CCC(CC1)N[C@@H]([C@H](NC1CCCCC1)c1ccccc1)c1ccccc1 DMKKIUIRZXFPDW-CLJLJLNGSA-N 0.000 description 1
- BTHYVQUNQHWNLS-HZPDHXFCSA-N (1r,2r)-n,n'-dimethyl-1,2-diphenylethane-1,2-diamine Chemical compound C1([C@@H](NC)[C@H](NC)C=2C=CC=CC=2)=CC=CC=C1 BTHYVQUNQHWNLS-HZPDHXFCSA-N 0.000 description 1
- WDYGPMAMBXJESZ-GOSISDBHSA-N (2r)-1,1-bis(4-methoxyphenyl)-3-methylbutane-1,2-diamine Chemical compound C1=CC(OC)=CC=C1C(N)([C@H](N)C(C)C)C1=CC=C(OC)C=C1 WDYGPMAMBXJESZ-GOSISDBHSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 239000004912 1,5-cyclooctadiene Substances 0.000 description 1
- JELCTTFEQUFDER-UHFFFAOYSA-N 1-(4-methoxyphenyl)-3-methylbutane-1,2-diamine Chemical compound COC1=CC=C(C(N)C(N)C(C)C)C=C1 JELCTTFEQUFDER-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- QTVYDTSEMXDJQW-YUMQZZPRSA-N CCN[C@@H](C)[C@H](C)NCC Chemical compound CCN[C@@H](C)[C@H](C)NCC QTVYDTSEMXDJQW-YUMQZZPRSA-N 0.000 description 1
- LSOOREOZDAALJZ-HMMHJWGRSA-N CN[C@@H]([C@H](NC)C1C(CCCC1)C)C1C(CCCC1)C Chemical compound CN[C@@H]([C@H](NC)C1C(CCCC1)C)C1C(CCCC1)C LSOOREOZDAALJZ-HMMHJWGRSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- LZWQNOHZMQIFBX-UHFFFAOYSA-N lithium;2-methylpropan-2-olate Chemical compound [Li+].CC(C)(C)[O-] LZWQNOHZMQIFBX-UHFFFAOYSA-N 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- UOPFIWYXBIHPIP-UHFFFAOYSA-N n-(2-amino-1,2-diphenylethyl)-4-methylbenzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(C=1C=CC=CC=1)C(N)C1=CC=CC=C1 UOPFIWYXBIHPIP-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
で表される光学活性ジアミン、ホスフィンが配位していないルテニウム錯体及び塩基の存在下に、ホスフィンを添加せずに、水素化することを特徴とする光学活性3−キヌクリジノールの製造方法に関するものである。
で表されるジアミンであることを特徴とするものである。
試験管に3−キヌクリジノン0.5g(4mmol)、ナトリウムメトキシドの28%メタノール溶液 1.55g(0.6mmol)、[{RuCl2(η6−C6H6)}2]10mg(20μmol、Ru原子40μ当量)、(1R,2R)−1,2−ビス[(3−トリフルオロメチル)フェニル]−1,2−エタンジアミン(以下、「(1R,2R)−FDPEN」と略称)30mg(85μmol)をそれぞれ量り取り、メタノール6mlに溶解させた。試験管をオートクレーブに入れ、水素ガスにより置換した後、3.6MPaに加圧した。室温で18時間撹拌、反応させた。反応液を減圧下に濃縮し粗生成物を得た。得られた生成物をGLC及びHPLC により分析したところ、3−キヌクリジノンは検出されず、得られた3−キヌクリジノールの鏡像体過剰率は48%ee(R)であった。
試験管に3−キヌクリジノン0.5g(4mmol)、カリウム(tert−ブトキシド)13.5mg(0.12mmol)、[{RuCl2(η6−C6H6)}2]10mg(20μmol、Ru原子40μ当量)、(1S,2S)−シクロヘキサン−1,2−ジアミン(「(1S,2S)−DACH」と略称)9.7mg(85μmol)をそれぞれ量り取り、エタノール6mlに溶解させた。試験管をオートクレーブに入れ、水素ガスにより置換した後、3.6MPaに加圧した。室温で15時間撹拌、反応させた。反応液を減圧下に濃縮し粗生成物を得た。得られた生成物をGLC及びHPLC により分析したところ、3−キヌクリジノンは検出されず、得られた3−キヌクリジノールの鏡像体過剰率は58%ee(S)であった。
試験管に3−キヌクリジノン 0.5g(4mmol)、[RuCl{(R,R)−TsNCH(C6H5)CH(C6H5)NH}{(1R,2R)−N−p−トルエンスルホニル−1,2−ジフェニルエチレンジアミン}(η6−p−シメン)ルテニウム(以下、[RuCl{(1R,2R)−TsDPEN}(η6−p−シメン)]と略称,関東化学(株)製)13mg (20μmol)、カリウム(tert−ブトキシド)15mg (0.13mmol)を量り取り、メタノール6mlに溶解させた。試験管内に窒素を満たした後、オートクレーブに入れ、オートクレーブ内を窒素置換し、続いて水素置換した。水素圧4.0MPa、室温で20時間反応させた。3−キヌクリジノールへの転化率は100%で、得られた3−キヌクリジノールの鏡像体過剰率は24%(R)であった。
光学活性ジアミンとして、(1R,2R)−(+)−MeFDPENに替えて(R)−1,1’−ビス(p−メトキシフェニル)−2−イソプロピル−1,2−エタンジアミン(以下、(R)−DAIPENと略称,関東化学(株)製)を使用した以外は、実施例1と同様に反応を行なった。91時間後には3−キヌクリジノンが消失しており、得られた3−キヌクリジノールの鏡像体過剰率は19%(R)であった。
Claims (2)
- 3−キヌクリジノンを水素化して光学活性3−キヌクリジノールを得る際に、一般式(3)
で表される光学活性ジアミン、ホスフィンが配位していないルテニウム錯体及び塩基の存在下に、ホスフィンを添加せずに、水素化することを特徴とする光学活性3−キヌクリジノールの製造方法。 - 光学活性ジアミンが、一般式(4)
(ただし、R3及びR4は前記と同じで、R5及びR6は同一であっても異なってもよく、置換基を有するフェニル基またはシクロアルキル基、もしくはR5とR6が一緒になって置換基を有する脂環式環を形成することを示し、*は不斉中心を示す)
で表されるジアミンであることを特徴とする請求項1に記載の光学活性3−キヌクリジノールの製造方法。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2008035673A JP5330706B2 (ja) | 2007-02-23 | 2008-02-18 | 光学活性3−キヌクリジノールの製造方法 |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2007043419 | 2007-02-23 | ||
JP2007043419 | 2007-02-23 | ||
JP2008035673A JP5330706B2 (ja) | 2007-02-23 | 2008-02-18 | 光学活性3−キヌクリジノールの製造方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2008231097A JP2008231097A (ja) | 2008-10-02 |
JP5330706B2 true JP5330706B2 (ja) | 2013-10-30 |
Family
ID=39904320
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2008035673A Expired - Fee Related JP5330706B2 (ja) | 2007-02-23 | 2008-02-18 | 光学活性3−キヌクリジノールの製造方法 |
Country Status (1)
Country | Link |
---|---|
JP (1) | JP5330706B2 (ja) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN111454258B (zh) * | 2020-05-28 | 2021-07-20 | 中山奕安泰医药科技有限公司 | 索非那新中间体的制备方法 |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0916637B1 (en) * | 1995-12-06 | 2005-04-20 | Japan Science and Technology Agency | Process for preparating optically active compounds |
JP4052702B2 (ja) * | 1997-12-26 | 2008-02-27 | 独立行政法人科学技術振興機構 | 光学活性アルコール類の製造方法 |
JP2003277380A (ja) * | 2002-03-20 | 2003-10-02 | Kawaken Fine Chem Co Ltd | 光学活性3−キヌクリジノールの製造方法 |
JP2005306804A (ja) * | 2004-04-23 | 2005-11-04 | Takasago Internatl Corp | 光学活性3−キヌクリジノールの製造方法 |
JP4490211B2 (ja) * | 2004-08-27 | 2010-06-23 | 高砂香料工業株式会社 | 光学活性3−キヌクリジノール類の製造方法 |
-
2008
- 2008-02-18 JP JP2008035673A patent/JP5330706B2/ja not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
JP2008231097A (ja) | 2008-10-02 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US8962839B2 (en) | Chiral spiro-pyridylamidophosphine ligand compound, synthesis method therefor and application thereof | |
US20130041151A1 (en) | Ruthenium complex and method for preparing optically active alcohol compound | |
JPH11189600A (ja) | ルテニウム錯体とこれを触媒とするアルコール化合物 の製造方法 | |
EP1276745B1 (en) | Ruthenium-diphosphine complexes and their use as catalysts | |
WO2012105431A1 (ja) | β-フルオロアルコール類の製造方法 | |
US7601667B2 (en) | Sulfonate catalyst and method of producing alcohol compound using the same | |
US9255049B2 (en) | Ruthenium complex and method for preparing optically active alcohol compounds using the same as a catalyst | |
EP2264000B1 (en) | Method for producing optically active aminoalcohol compound using ruthenium compound | |
JP6018046B2 (ja) | ケトエステル類の水素化のためのプロセス | |
JP5330706B2 (ja) | 光学活性3−キヌクリジノールの製造方法 | |
US5780692A (en) | Process for producing optically active benzhydrol compounds | |
EP1601635B1 (en) | Process for producing optically active alcohol in the presence of rhodium, a chiral ferrocenyldiphosphine and an optically active diamine | |
US20150329452A1 (en) | Method for producing optically active isopulegol and optically active menthol | |
JP4286486B2 (ja) | ルテニウム化合物、ジアミン配位子および光学活性アルコールの製造方法 | |
US7649117B2 (en) | Process of preparing optically active β-hydroxycarboxylic acid derivative | |
JP3569280B1 (ja) | 光学活性アルコールの製造方法 | |
CN114605272A (zh) | 一种(r)-氟西汀及其衍生物的制备方法 | |
US9029540B2 (en) | Ruthenium catalysts and their use for asymmetric reduction of ketones | |
US8558033B2 (en) | Process for producing optically active aliphatic fluoroalcohol | |
JP4209620B2 (ja) | 光学活性なトランス−2−アミノシクロアルカノール又はその塩の製造方法 | |
JPH054948A (ja) | 光学活性アミノアルコールおよびその中間体の製造方法 | |
US20120309997A1 (en) | Enantiomerically Enriched Aminodiphosphines as Ligands for the Preparation of Catalysts for Asymmetric Synthesis | |
JP5303311B2 (ja) | 光学活性含フッ素アルキニル化生成物の製造方法 | |
JP5762288B2 (ja) | アリルアミンの製造方法 | |
JP2005306804A (ja) | 光学活性3−キヌクリジノールの製造方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20100903 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20130205 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20130322 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20130514 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20130517 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20130723 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20130726 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 5330706 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
LAPS | Cancellation because of no payment of annual fees |