JP2009522229A - 2,6−trans−ジメチルモルホリンのラセミ分離 - Google Patents
2,6−trans−ジメチルモルホリンのラセミ分離 Download PDFInfo
- Publication number
- JP2009522229A JP2009522229A JP2008547943A JP2008547943A JP2009522229A JP 2009522229 A JP2009522229 A JP 2009522229A JP 2008547943 A JP2008547943 A JP 2008547943A JP 2008547943 A JP2008547943 A JP 2008547943A JP 2009522229 A JP2009522229 A JP 2009522229A
- Authority
- JP
- Japan
- Prior art keywords
- dimethylmorpholine
- trans
- salt
- optically active
- mandelic acid
- 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.)
- Granted
Links
- HNVIQLPOGUDBSU-WDSKDSINSA-N (2s,6s)-2,6-dimethylmorpholine Chemical compound C[C@H]1CNC[C@H](C)O1 HNVIQLPOGUDBSU-WDSKDSINSA-N 0.000 title 1
- 238000000926 separation method Methods 0.000 title 1
- HNVIQLPOGUDBSU-PHDIDXHHSA-N (2r,6r)-2,6-dimethylmorpholine Chemical compound C[C@@H]1CNC[C@@H](C)O1 HNVIQLPOGUDBSU-PHDIDXHHSA-N 0.000 claims abstract description 35
- 150000003839 salts Chemical class 0.000 claims abstract description 29
- 238000000034 method Methods 0.000 claims abstract description 23
- IWYDHOAUDWTVEP-SSDOTTSWSA-N (R)-mandelic acid Chemical compound OC(=O)[C@H](O)C1=CC=CC=C1 IWYDHOAUDWTVEP-SSDOTTSWSA-N 0.000 claims abstract description 8
- 238000004519 manufacturing process Methods 0.000 claims abstract description 6
- HNVIQLPOGUDBSU-UHFFFAOYSA-N 2,6-dimethylmorpholine Chemical compound CC1CNCC(C)O1 HNVIQLPOGUDBSU-UHFFFAOYSA-N 0.000 claims abstract 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 15
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 claims description 14
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 claims description 14
- 229960002510 mandelic acid Drugs 0.000 claims description 14
- IWYDHOAUDWTVEP-ZETCQYMHSA-N (S)-mandelic acid Chemical compound OC(=O)[C@@H](O)C1=CC=CC=C1 IWYDHOAUDWTVEP-ZETCQYMHSA-N 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 239000012429 reaction media Substances 0.000 claims description 2
- 230000001376 precipitating effect Effects 0.000 claims 1
- 230000003287 optical effect Effects 0.000 description 17
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000013078 crystal Substances 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- VNEBWJSWMVTSHK-UHFFFAOYSA-L disodium;3-hydroxynaphthalene-2,7-disulfonate Chemical compound [Na+].[Na+].C1=C(S([O-])(=O)=O)C=C2C=C(S([O-])(=O)=O)C(O)=CC2=C1 VNEBWJSWMVTSHK-UHFFFAOYSA-L 0.000 description 7
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- IWYDHOAUDWTVEP-SSDOTTSWSA-M (R)-mandelate Chemical compound [O-]C(=O)[C@H](O)C1=CC=CC=C1 IWYDHOAUDWTVEP-SSDOTTSWSA-M 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 238000012916 structural analysis Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- HNVIQLPOGUDBSU-LWOQYNTDSA-N (2r)-2,6-dimethylmorpholine Chemical compound CC1CNC[C@@H](C)O1 HNVIQLPOGUDBSU-LWOQYNTDSA-N 0.000 description 1
- HNVIQLPOGUDBSU-OLQVQODUSA-N (2s,6r)-2,6-dimethylmorpholine Chemical compound C[C@H]1CNC[C@@H](C)O1 HNVIQLPOGUDBSU-OLQVQODUSA-N 0.000 description 1
- PLYTVAFAKDFFKM-ZCFIWIBFSA-N (3r)-3,4-dimethylmorpholine Chemical compound C[C@@H]1COCCN1C PLYTVAFAKDFFKM-ZCFIWIBFSA-N 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- PLYTVAFAKDFFKM-UHFFFAOYSA-N 3,4-dimethylmorpholine Chemical compound CC1COCCN1C PLYTVAFAKDFFKM-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
- 244000144725 Amygdalus communis Species 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
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011734 sodium 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
- 238000000967 suction filtration Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/027—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
【選択図】なし
Description
Licandroら, Gazzetta Chimica Italiana 1997, 127, 815-817
初めにD-マンデル酸(330.4g、2.174mol)をイソプロパノール(2 l)中に供給し、まず酢酸(130.4g、2.174mol)を、次にtrans-2,6-ジメチルモルホリン(trans-DiMeMo、500g、4.348mol)を速やかに滴下して加えて混合した。この過程で、混合物の温度は45℃に上昇した。透明な溶液に、R,S,S塩2を種晶として加え、そして室温にて一晩放置した。翌日、その混合物を攪拌しながら10℃に冷却しそして沈降した残留物を吸引濾過した。単離したR,S,S塩2(400g(湿)、34%)中に結合したS,S-DiMeMoは74%eeの光学純度を有していた。その塩をイソプロパノール(1 l)中で煮沸し、室温に冷却しそしてR,S,S塩2の1つの結晶を種晶として加えた。混合物を室温にて一晩放置しそして翌日再び吸引濾過した。350g(30%、湿)のR,S,S塩2を得た;それに結合したS,S-DiMeMoは97.7%eeの光学純度を有した。その塩を再び加温条件(70℃)下でイソプロパノール(1 l)に溶解しそして室温にて一晩放置した。再び、その混合物にR,S,S塩2の1つの結晶を種晶として加えそして一晩放置した。沈降した塩を吸引濾過して取り出しそして乾燥室内で乾燥した。266.5g(23%)のR,S,S塩2を得た;それに結合したS,S-DiMeMoは98.3%eeの光学純度を有した。R,S,S塩2の融点は134℃であった。
D-マンデル酸塩(R,S,S塩2、266.5g、1mol)を20%水酸化ナトリウム溶液(400ml)に溶解し、50℃にて1時間攪拌した。これによって透明な溶液を得た。浴温を120℃に上昇させ、遊離したS,S-DiMeMoを蒸留装置により水との共沸混合物で(100℃にて)留出させた。ほぼ300mlの凝縮液が留出した後に、蒸留受器を室温に冷却し、10%HClを用いて酸性化した。沈降したマンデル酸を吸引濾過して取り出し、減圧下で乾燥した。光学純度の分析結果はD-マンデル酸が全てラセミ化していることを示した。
光学純度27.8%ee(S,S:R,R=36:64)のR,R-DiMeMoを、a.で得たR,S,S塩2の母液から、b.に概説した方法により遊離した。全体で、312g(74%)の混合物を得た。
L-マンデル酸塩(S,R,R塩2、274g、1.03mol)を水(400ml)に溶解しそして濃塩酸を加えてpH1.5とした。その混合物を1℃に冷却しそして数個のS-マンデル酸の結晶を種晶として加えた。その混合物を0℃にてさらに2時間攪拌し、沈降した結晶スラリーを吸引濾過した。フィルター残留物を氷水(100ml)を用いて洗浄し、50℃にて減圧下で乾燥した。86g(57%)のL-マンデル酸を得た。これは分析によると光学的に純粋であった。
Claims (7)
- 光学活性trans-2,6-ジメチルモルホリンを製造する方法であって、(i)ラセミtrans-2,6-ジメチルモルホリンを光学活性マンデル酸と反応させるステップ、(ii)光学活性マンデル酸とtrans-2,6-ジメチルモルホリンの1つのエナンチオマーとから形成された塩をtrans-2,6-ジメチルモルホリンの他のエナンチオマーから取り出すステップ、および(iii)所望の光学活性trans-2,6-ジメチルモルホリンを単離するステップによる、前記方法。
- 前記の取り出すステップ(ii)を反応媒質から塩を沈降させることにより行う、請求項1に記載の方法。
- 反応をイソプロパノール中で行う、請求項1に記載の方法。
- 0.5モルまでの光学活性マンデル酸をラセミtrans-2,6-ジメチルモルホリン1モル当たりに用いる、請求項1に記載の方法。
- 0.5モルまでの酢酸を、光学活性マンデル酸の他に加える、請求項4に記載の方法。
- S,S-trans-2,6-ジメチルモルホリンをD-マンデル酸とともに沈降させる、請求項1に記載の方法。
- R,R-trans-2,6-ジメチルモルホリンをL-マンデル酸とともに沈降させる、請求項1に記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102005063192A DE102005063192A1 (de) | 2005-12-30 | 2005-12-30 | Racematspaltung von 2,6-trans-Dimethyl-morpholin |
DE102005063192.4 | 2005-12-30 | ||
PCT/EP2006/069862 WO2007077118A2 (de) | 2005-12-30 | 2006-12-18 | Racematspaltung von 2,6-trans-dimethylmorpholin |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2013184614A Division JP2014012713A (ja) | 2005-12-30 | 2013-09-06 | 2,6−trans−ジメチルモルホリンのラセミ分離 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2009522229A true JP2009522229A (ja) | 2009-06-11 |
JP5714213B2 JP5714213B2 (ja) | 2015-05-07 |
Family
ID=38135789
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2008547943A Expired - Fee Related JP5714213B2 (ja) | 2005-12-30 | 2006-12-18 | 2,6−trans−ジメチルモルホリンのラセミ分離 |
JP2013184614A Pending JP2014012713A (ja) | 2005-12-30 | 2013-09-06 | 2,6−trans−ジメチルモルホリンのラセミ分離 |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2013184614A Pending JP2014012713A (ja) | 2005-12-30 | 2013-09-06 | 2,6−trans−ジメチルモルホリンのラセミ分離 |
Country Status (8)
Country | Link |
---|---|
US (1) | US7829702B2 (ja) |
EP (1) | EP1968960B1 (ja) |
JP (2) | JP5714213B2 (ja) |
CN (1) | CN101331121B (ja) |
AT (1) | ATE469137T1 (ja) |
DE (2) | DE102005063192A1 (ja) |
ES (1) | ES2344474T3 (ja) |
WO (1) | WO2007077118A2 (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2014012713A (ja) * | 2005-12-30 | 2014-01-23 | Basf Se | 2,6−trans−ジメチルモルホリンのラセミ分離 |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103275031A (zh) * | 2013-05-14 | 2013-09-04 | 泰州锦鸿医药科技有限公司 | 一种制备光学纯的福沙匹坦中间体的方法 |
US10416213B2 (en) * | 2014-10-29 | 2019-09-17 | Nokomis, Inc. | Ultra-sensitive, ultra-low power RF field sensor |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2003514888A (ja) * | 1999-11-25 | 2003-04-22 | ビーエーエスエフ アクチェンゲゼルシャフト | 光学活性アミンの製造方法 |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2822326A1 (de) | 1978-05-22 | 1979-11-29 | Basf Ag | Antimykotische mittel |
DK149624C (da) * | 1983-03-07 | 1987-02-02 | Ferrosan As | Fremgangsmaade til fremstilling af (+)-trans-3-((4-methoxyphenoxy)-methyl)-1-methyl-4-phenylpiperidin eller et farmaceutisk acceptabelt salt heraf ud fra en blanding af enantiomererne |
CA2162400A1 (en) | 1993-05-28 | 1994-12-08 | William M. Snyder | Process for preparing and resolving 2-phenyl-3-aminopiperidine |
US20040039206A1 (en) * | 2001-11-13 | 2004-02-26 | Moher Eric David | Process for resolving racemic mixtures of piperidine derivatives |
DE102005063192A1 (de) * | 2005-12-30 | 2007-07-05 | Basf Ag | Racematspaltung von 2,6-trans-Dimethyl-morpholin |
-
2005
- 2005-12-30 DE DE102005063192A patent/DE102005063192A1/de not_active Withdrawn
-
2006
- 2006-12-18 AT AT06830698T patent/ATE469137T1/de active
- 2006-12-18 CN CN2006800470091A patent/CN101331121B/zh not_active Expired - Fee Related
- 2006-12-18 US US12/159,504 patent/US7829702B2/en not_active Expired - Fee Related
- 2006-12-18 DE DE502006007059T patent/DE502006007059D1/de active Active
- 2006-12-18 EP EP06830698A patent/EP1968960B1/de active Active
- 2006-12-18 ES ES06830698T patent/ES2344474T3/es active Active
- 2006-12-18 JP JP2008547943A patent/JP5714213B2/ja not_active Expired - Fee Related
- 2006-12-18 WO PCT/EP2006/069862 patent/WO2007077118A2/de active Application Filing
-
2013
- 2013-09-06 JP JP2013184614A patent/JP2014012713A/ja active Pending
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2003514888A (ja) * | 1999-11-25 | 2003-04-22 | ビーエーエスエフ アクチェンゲゼルシャフト | 光学活性アミンの製造方法 |
Non-Patent Citations (3)
Title |
---|
JPN5008022213; EMANUELA LICANDRO: TETRAHEDRON ASYMMETRY V11, 2000, P975-980 * |
JPN6011042700; 光学異性体の分離〔季刊 化学総説 No.6〕 3刷, 19990610, p.45-54, 株式会社 学会出版センター * |
JPN6012041724; LICANDRO,E. et al: 'Asymmetric synthesis of (-)-(2R,6R)-2,6-dimethylmorpholine' Tetrahedron: Asymmetry Vol.6, No.8, 1995, p.1891-1894 * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2014012713A (ja) * | 2005-12-30 | 2014-01-23 | Basf Se | 2,6−trans−ジメチルモルホリンのラセミ分離 |
Also Published As
Publication number | Publication date |
---|---|
JP2014012713A (ja) | 2014-01-23 |
US7829702B2 (en) | 2010-11-09 |
WO2007077118A3 (de) | 2007-10-11 |
ES2344474T3 (es) | 2010-08-27 |
DE502006007059D1 (de) | 2010-07-08 |
JP5714213B2 (ja) | 2015-05-07 |
CN101331121B (zh) | 2011-07-13 |
DE102005063192A1 (de) | 2007-07-05 |
US20090012289A1 (en) | 2009-01-08 |
CN101331121A (zh) | 2008-12-24 |
ATE469137T1 (de) | 2010-06-15 |
WO2007077118A2 (de) | 2007-07-12 |
EP1968960B1 (de) | 2010-05-26 |
EP1968960A2 (de) | 2008-09-17 |
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