JPS6241501B2 - - Google Patents
Info
- Publication number
- JPS6241501B2 JPS6241501B2 JP54122135A JP12213579A JPS6241501B2 JP S6241501 B2 JPS6241501 B2 JP S6241501B2 JP 54122135 A JP54122135 A JP 54122135A JP 12213579 A JP12213579 A JP 12213579A JP S6241501 B2 JPS6241501 B2 JP S6241501B2
- Authority
- JP
- Japan
- Prior art keywords
- hexane
- cis
- azabicyclo
- trans
- cyano
- 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
Links
- 239000000203 mixture Substances 0.000 claims abstract description 21
- JFUYLMCSIHJLOX-UHFFFAOYSA-N 3-azabicyclo[3.1.0]hexane-2-carbonitrile Chemical compound N#CC1NCC2CC12 JFUYLMCSIHJLOX-UHFFFAOYSA-N 0.000 claims abstract description 10
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical class CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 claims abstract description 7
- 238000000605 extraction Methods 0.000 claims abstract description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 42
- 150000003839 salts Chemical class 0.000 claims description 32
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 8
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 8
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims description 7
- 229940092714 benzenesulfonic acid Drugs 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000002244 precipitate Substances 0.000 claims description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 2
- 230000001376 precipitating effect Effects 0.000 claims description 2
- NIXKBAZVOQAHGC-UHFFFAOYSA-N phenylmethanesulfonic acid Chemical class OS(=O)(=O)CC1=CC=CC=C1 NIXKBAZVOQAHGC-UHFFFAOYSA-N 0.000 claims 1
- 150000008107 benzenesulfonic acids Chemical class 0.000 abstract 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- 238000000926 separation method Methods 0.000 description 11
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 239000007787 solid Substances 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 150000008054 sulfonate salts Chemical class 0.000 description 6
- XZKBYNGLKZFLOW-UHFFFAOYSA-N 3-azabicyclo[3.1.0]hexane-2-carbonitrile;4-methylbenzenesulfonic acid Chemical compound N#CC1NCC2CC12.CC1=CC=C(S(O)(=O)=O)C=C1 XZKBYNGLKZFLOW-UHFFFAOYSA-N 0.000 description 5
- 150000002825 nitriles Chemical class 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000006317 isomerization reaction Methods 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- JBDOTWVUXVXVDR-UHFFFAOYSA-N 3-azoniabicyclo[3.1.0]hexane-2-carboxylate Chemical compound OC(=O)C1NCC2CC12 JBDOTWVUXVXVDR-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000001030 gas--liquid chromatography Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
- FICQFRCPSFCFBY-UHFFFAOYSA-N 2-[bis(methylsulfanyl)methylidene]propanedinitrile Chemical compound CSC(SC)=C(C#N)C#N FICQFRCPSFCFBY-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
- MPCUXJQXCFGFLG-UHFFFAOYSA-N 2-oxo-3-azabicyclo[3.1.0]hexane-4-carbonitrile Chemical compound O=C1NC(C#N)C2CC12 MPCUXJQXCFGFLG-UHFFFAOYSA-N 0.000 description 1
- QRDSDKAGXMWBID-UHFFFAOYSA-N 5-azabicyclo[3.1.0]hexane Chemical compound C1CCN2CC21 QRDSDKAGXMWBID-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000005341 cation exchange Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000001212 derivatisation Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000011833 salt mixture Substances 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- -1 triethyloxonium tetrafluoroborate Chemical compound 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/52—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring condensed with a ring other than six-membered
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7838331 | 1978-09-27 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5545691A JPS5545691A (en) | 1980-03-31 |
| JPS6241501B2 true JPS6241501B2 (c_deeref_Disk_and_Scratch_Disk_Pools_and_Their_Defaults.html) | 1987-09-03 |
Family
ID=10499940
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP12213579A Granted JPS5545691A (en) | 1978-09-27 | 1979-09-25 | 33azabicyclo*3*1*0*hexane derivative and its manufacture |
Country Status (12)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6198154U (c_deeref_Disk_and_Scratch_Disk_Pools_and_Their_Defaults.html) * | 1984-12-05 | 1986-06-24 | ||
| EP2481737A1 (en) * | 2008-06-24 | 2012-08-01 | Merck Sharp & Dohme Corp. | Biocatalytic processes for the preparation of substantially stereomerically pure fused bicyclic proline compounds |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5147691B2 (c_deeref_Disk_and_Scratch_Disk_Pools_and_Their_Defaults.html) * | 1974-02-08 | 1976-12-16 | ||
| GB1567153A (en) * | 1975-09-16 | 1980-05-14 | Shell Int Research | Method of sterilizing male anthers of angiosperms |
| GB2015515B (en) * | 1978-03-01 | 1982-09-22 | Shell Int Research | 3-azabicyclo(3.1.0)hexane derivatives |
-
1979
- 1979-08-27 CA CA000334496A patent/CA1116615A/en not_active Expired
- 1979-09-04 US US06/071,980 patent/US4228081A/en not_active Expired - Lifetime
- 1979-09-17 AT AT79200519T patent/ATE1315T1/de not_active IP Right Cessation
- 1979-09-17 EP EP79200519A patent/EP0009290B1/en not_active Expired
- 1979-09-17 DE DE7979200519T patent/DE2963303D1/de not_active Expired
- 1979-09-25 BR BR7906139A patent/BR7906139A/pt unknown
- 1979-09-25 ES ES484423A patent/ES484423A1/es not_active Expired
- 1979-09-25 AU AU51157/79A patent/AU524914B2/en not_active Ceased
- 1979-09-25 ZA ZA00795096A patent/ZA795096B/xx unknown
- 1979-09-25 IL IL58312A patent/IL58312A/xx unknown
- 1979-09-25 DK DK401879A patent/DK401879A/da not_active Application Discontinuation
- 1979-09-25 JP JP12213579A patent/JPS5545691A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| ATE1315T1 (de) | 1982-07-15 |
| AU5115779A (en) | 1980-03-06 |
| JPS5545691A (en) | 1980-03-31 |
| IL58312A0 (en) | 1979-12-30 |
| EP0009290B1 (en) | 1982-07-07 |
| CA1116615A (en) | 1982-01-19 |
| IL58312A (en) | 1982-08-31 |
| ZA795096B (en) | 1980-09-24 |
| DK401879A (da) | 1980-03-28 |
| EP0009290A1 (en) | 1980-04-02 |
| ES484423A1 (es) | 1980-05-16 |
| AU524914B2 (en) | 1982-10-07 |
| DE2963303D1 (en) | 1982-08-26 |
| US4228081A (en) | 1980-10-14 |
| BR7906139A (pt) | 1980-05-27 |
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