JPS5824545A - （±）−１−（１−ナフチル）エチルアミンの光学分割法 - Google Patents
（±）−１−（１−ナフチル）エチルアミンの光学分割法Info
- Publication number
- JPS5824545A JPS5824545A JP12312481A JP12312481A JPS5824545A JP S5824545 A JPS5824545 A JP S5824545A JP 12312481 A JP12312481 A JP 12312481A JP 12312481 A JP12312481 A JP 12312481A JP S5824545 A JPS5824545 A JP S5824545A
- Authority
- JP
- Japan
- Prior art keywords
- ethylamine
- naphthyl
- optical resolution
- optically active
- 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
- 230000003287 optical effect Effects 0.000 title claims abstract description 16
- RTCUCQWIICFPOD-UHFFFAOYSA-N 1-naphthalen-1-ylethanamine Chemical compound C1=CC=C2C(C(N)C)=CC=CC2=C1 RTCUCQWIICFPOD-UHFFFAOYSA-N 0.000 title description 5
- PUANNVQABXUYKU-NEPJUHHUSA-N (1r,2s)-2-benzamidocyclohexane-1-carboxylic acid Chemical compound OC(=O)[C@@H]1CCCC[C@@H]1NC(=O)C1=CC=CC=C1 PUANNVQABXUYKU-NEPJUHHUSA-N 0.000 claims abstract description 8
- 238000000034 method Methods 0.000 claims description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract description 21
- 239000003795 chemical substances by application Substances 0.000 abstract description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 6
- 239000002904 solvent Substances 0.000 abstract description 4
- 239000002253 acid Substances 0.000 abstract description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 abstract 3
- 239000000919 ceramic Substances 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 10
- 150000003839 salts Chemical class 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
- KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- NZNMSOFKMUBTKW-UHFFFAOYSA-M cyclohexanecarboxylate Chemical compound [O-]C(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-M 0.000 description 2
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- -1 By using 1-glopanol Substances 0.000 description 1
- 235000001258 Cinchona calisaya Nutrition 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
- 150000007513 acids Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- AJPOREWXLFKIOC-UHFFFAOYSA-N benzamide;cyclohexanecarboxylic acid Chemical compound NC(=O)C1=CC=CC=C1.OC(=O)C1CCCCC1 AJPOREWXLFKIOC-UHFFFAOYSA-N 0.000 description 1
- RRKTZKIUPZVBMF-IBTVXLQLSA-N brucine Chemical compound O([C@@H]1[C@H]([C@H]2C3)[C@@H]4N(C(C1)=O)C=1C=C(C(=CC=11)OC)OC)CC=C2CN2[C@@H]3[C@]41CC2 RRKTZKIUPZVBMF-IBTVXLQLSA-N 0.000 description 1
- RRKTZKIUPZVBMF-UHFFFAOYSA-N brucine Natural products C1=2C=C(OC)C(OC)=CC=2N(C(C2)=O)C3C(C4C5)C2OCC=C4CN2C5C31CC2 RRKTZKIUPZVBMF-UHFFFAOYSA-N 0.000 description 1
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Natural products OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 description 1
- KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 description 1
- 229960002179 ephedrine Drugs 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- KDFFXYVOTKKBDI-UHFFFAOYSA-N n-ethylnaphthalen-1-amine Chemical compound C1=CC=C2C(NCC)=CC=CC2=C1 KDFFXYVOTKKBDI-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 229960000948 quinine Drugs 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12312481A JPS5824545A (ja) | 1981-08-07 | 1981-08-07 | （±）−１−（１−ナフチル）エチルアミンの光学分割法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12312481A JPS5824545A (ja) | 1981-08-07 | 1981-08-07 | （±）−１−（１−ナフチル）エチルアミンの光学分割法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5824545A true JPS5824545A (ja) | 1983-02-14 |
| JPS6139299B2 JPS6139299B2 (enrdf_load_stackoverflow) | 1986-09-03 |
Family
ID=14852773
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP12312481A Granted JPS5824545A (ja) | 1981-08-07 | 1981-08-07 | （±）−１−（１−ナフチル）エチルアミンの光学分割法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5824545A (enrdf_load_stackoverflow) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6133164A (ja) * | 1984-07-25 | 1986-02-17 | Nippon Chemiphar Co Ltd | プロピオン酸誘導体の光学分割方法 |
| JPS6354342A (ja) * | 1986-08-26 | 1988-03-08 | Daicel Chem Ind Ltd | （±）−α−エチルベンジルアミンの光学分割方法 |
| JPS6354341A (ja) * | 1986-08-26 | 1988-03-08 | Daicel Chem Ind Ltd | 光学分割法 |
| US8575393B2 (en) | 2009-03-05 | 2013-11-05 | Cipla Limited | Process for the preparation of cinacalcet and salts thereof, and intermediates for use in the process |
-
1981
- 1981-08-07 JP JP12312481A patent/JPS5824545A/ja active Granted
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6133164A (ja) * | 1984-07-25 | 1986-02-17 | Nippon Chemiphar Co Ltd | プロピオン酸誘導体の光学分割方法 |
| JPS6354342A (ja) * | 1986-08-26 | 1988-03-08 | Daicel Chem Ind Ltd | （±）−α−エチルベンジルアミンの光学分割方法 |
| JPS6354341A (ja) * | 1986-08-26 | 1988-03-08 | Daicel Chem Ind Ltd | 光学分割法 |
| US8575393B2 (en) | 2009-03-05 | 2013-11-05 | Cipla Limited | Process for the preparation of cinacalcet and salts thereof, and intermediates for use in the process |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6139299B2 (enrdf_load_stackoverflow) | 1986-09-03 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPS5824545A (ja) | （±）−１−（１−ナフチル）エチルアミンの光学分割法 | |
| JPS6013736A (ja) | （±）−２−クロロプロピオン酸の光学分割法 | |
| JP3716376B2 (ja) | 光学分割剤およびそれを用いた光学活性３−アミノピロリジン誘導体の製造法 | |
| JP2830364B2 (ja) | 光学活性１―ベンジル―３―ヒドロキシピロリジンの製造方法 | |
| JPH07330732A (ja) | 光学活性な３−アミノ−１−ベンジルピペリジン誘導体 | |
| JPS6354342A (ja) | （±）−α−エチルベンジルアミンの光学分割方法 | |
| JP2574254B2 (ja) | 光学分割法 | |
| JP3284605B2 (ja) | 光学活性１−（１−ナフチル）エチルアミンの製造法 | |
| JP2884703B2 (ja) | 光学活性２―メチルピペラジンの製造法 | |
| JP2823679B2 (ja) | 光学活性２―メチルピペラジンの製造方法 | |
| JPS60104045A (ja) | （±）−１−（４−イソプロピルフエニル）エチルアミンの光学分割法 | |
| JPH0816084B2 (ja) | 光学活性フェニルエチルアミン誘導体の製造法 | |
| JPH0418058A (ja) | （±）―１―メチル―２―（４―クロロフェニル）エチルアミンの光学分割法 | |
| JP3284608B2 (ja) | 光学活性１−フェニルエチルアミン誘導体の製造法 | |
| JPS59110656A (ja) | 光学活性な１―フェニル―２―（パラ―トリル）エチルアミンの製造方法 | |
| JPS63165348A (ja) | 光学活性１−（２，５−ジメトキシフエニル）−２−アミノ−１−プロパノ−ルの製造方法 | |
| JPH0720915B2 (ja) | （±）−トランス−ペルメトリン酸の光学分割法 | |
| JPS6410509B2 (enrdf_load_stackoverflow) | ||
| JPS6213337B2 (enrdf_load_stackoverflow) | ||
| JPS625140B2 (enrdf_load_stackoverflow) | ||
| JPH08143515A (ja) | 光学活性１−（２，４−ジクロロフェニル）エチルアミンの製造法 | |
| JPH01308244A (ja) | （±）―２―ヒドロキシ―４―フェニルブタン酸の光学分割法 | |
| JPH10101629A (ja) | 光学活性酪酸誘導体の製造方法 | |
| JPH0481977B2 (enrdf_load_stackoverflow) | ||
| JPH0143731B2 (enrdf_load_stackoverflow) |