JPH0511114B2 - - Google Patents
Info
- Publication number
- JPH0511114B2 JPH0511114B2 JP18696385A JP18696385A JPH0511114B2 JP H0511114 B2 JPH0511114 B2 JP H0511114B2 JP 18696385 A JP18696385 A JP 18696385A JP 18696385 A JP18696385 A JP 18696385A JP H0511114 B2 JPH0511114 B2 JP H0511114B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- methoxy
- water
- mmol
- add
- 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 - Lifetime
Links
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 150000003939 benzylamines Chemical class 0.000 claims description 2
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 48
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
- 239000000243 solution Substances 0.000 description 21
- 238000003756 stirring Methods 0.000 description 19
- ZOOJUDGKEJGVNL-UHFFFAOYSA-N 2,2-diethoxy-n-[(4-methoxy-1,3-benzodioxol-5-yl)methyl]-n-methylethanamine Chemical compound CCOC(OCC)CN(C)CC1=CC=C2OCOC2=C1OC ZOOJUDGKEJGVNL-UHFFFAOYSA-N 0.000 description 18
- WAVPLRIDLAJQPK-UHFFFAOYSA-N n-(2,2-diethoxyethyl)-n-[(4-methoxy-1,3-benzodioxol-5-yl)methyl]-4-methylbenzenesulfonamide Chemical compound C=1C=C2OCOC2=C(OC)C=1CN(CC(OCC)OCC)S(=O)(=O)C1=CC=C(C)C=C1 WAVPLRIDLAJQPK-UHFFFAOYSA-N 0.000 description 13
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000005160 1H NMR spectroscopy Methods 0.000 description 11
- 238000001816 cooling Methods 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 9
- 239000013078 crystal Substances 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- DYHYOYFSCMNDMX-UHFFFAOYSA-N 4-methoxy-[1,3]dioxolo[4,5-g]isoquinoline Chemical compound C1=NC=C2C(OC)=C(OCO3)C3=CC2=C1 DYHYOYFSCMNDMX-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 5
- 229910003446 platinum oxide Inorganic materials 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- OOUVEYDKXFXWDO-UHFFFAOYSA-N 4-methoxy-1,3-benzodioxole-5-carbaldehyde Chemical compound C1=C(C=O)C(OC)=C2OCOC2=C1 OOUVEYDKXFXWDO-UHFFFAOYSA-N 0.000 description 4
- XXANNZJIZQTCBP-UHFFFAOYSA-N 4-methoxy-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinoline Chemical compound C1CN(C)CC2=C1C=C1OCOC1=C2OC XXANNZJIZQTCBP-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 238000010898 silica gel chromatography Methods 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 238000010531 catalytic reduction reaction Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- AKNNEGZIBPJZJG-MSOLQXFVSA-N (-)-noscapine Chemical compound CN1CCC2=CC=3OCOC=3C(OC)=C2[C@@H]1[C@@H]1C2=CC=C(OC)C(OC)=C2C(=O)O1 AKNNEGZIBPJZJG-MSOLQXFVSA-N 0.000 description 2
- WHKGCBPFRLDALQ-UHFFFAOYSA-N (4-methoxy-1,3-benzodioxol-5-yl)methanamine;hydrochloride Chemical compound Cl.C1=C(CN)C(OC)=C2OCOC2=C1 WHKGCBPFRLDALQ-UHFFFAOYSA-N 0.000 description 2
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 2
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 description 2
- XRSKRSVTUVLURN-UHFFFAOYSA-N 1,3-benzodioxol-4-ol Chemical compound OC1=CC=CC2=C1OCO2 XRSKRSVTUVLURN-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- VHRHNRJVCHFFIS-UHFFFAOYSA-N 2,2-diethoxy-n-[(4-methoxy-1,3-benzodioxol-5-yl)methyl]ethanamine Chemical compound CCOC(OCC)CNCC1=CC=C2OCOC2=C1OC VHRHNRJVCHFFIS-UHFFFAOYSA-N 0.000 description 2
- HJKLEAOXCZIMPI-UHFFFAOYSA-N 2,2-diethoxyethanamine Chemical compound CCOC(CN)OCC HJKLEAOXCZIMPI-UHFFFAOYSA-N 0.000 description 2
- ULZLPEAVQIMJFQ-UHFFFAOYSA-N 2,2-dimethoxy-n-[(4-methoxy-1,3-benzodioxol-5-yl)methyl]-n-methylethanamine Chemical compound COC(OC)CN(C)CC1=CC=C2OCOC2=C1OC ULZLPEAVQIMJFQ-UHFFFAOYSA-N 0.000 description 2
- QKWWDTYDYOFRJL-UHFFFAOYSA-N 2,2-dimethoxyethanamine Chemical compound COC(CN)OC QKWWDTYDYOFRJL-UHFFFAOYSA-N 0.000 description 2
- PWUWHBYHOLXLFW-UHFFFAOYSA-N 4-hydroxy-1,3-benzodioxole-5-carbaldehyde Chemical compound C1=C(C=O)C(O)=C2OCOC2=C1 PWUWHBYHOLXLFW-UHFFFAOYSA-N 0.000 description 2
- WXIAEQCTLGPQCD-UHFFFAOYSA-N 4-methoxy-6-methyl-7,8-dihydro-5h-[1,3]dioxolo[4,5-g]isoquinolin-8-ol Chemical compound OC1CN(C)CC2=C1C=C1OCOC1=C2OC WXIAEQCTLGPQCD-UHFFFAOYSA-N 0.000 description 2
- -1 4-methylenedioxybenzyl Chemical group 0.000 description 2
- OLTIRXNFXDAUEC-UHFFFAOYSA-N 5-[[2,2-dimethoxyethyl(methyl)amino]methyl]-1,3-benzodioxol-4-ol Chemical compound COC(OC)CN(C)CC1=CC=C2OCOC2=C1O OLTIRXNFXDAUEC-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- AKNNEGZIBPJZJG-UHFFFAOYSA-N alpha-noscapine Natural products CN1CCC2=CC=3OCOC=3C(OC)=C2C1C1C2=CC=C(OC)C(OC)=C2C(=O)O1 AKNNEGZIBPJZJG-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- PERWGDOWASWOKM-UHFFFAOYSA-N n-[(4-methoxy-1,3-benzodioxol-5-yl)methyl]-4-methylbenzenesulfonamide Chemical compound COC1=C2OCOC2=CC=C1CNS(=O)(=O)C1=CC=C(C)C=C1 PERWGDOWASWOKM-UHFFFAOYSA-N 0.000 description 2
- VQQQKJDBFHRLPU-UHFFFAOYSA-N n-[(4-methoxy-1,3-benzodioxol-5-yl)methylidene]hydroxylamine Chemical compound C1=C(C=NO)C(OC)=C2OCOC2=C1 VQQQKJDBFHRLPU-UHFFFAOYSA-N 0.000 description 2
- PLPRGLOFPNJOTN-UHFFFAOYSA-N narcotine Natural products COc1ccc2C(OC(=O)c2c1OC)C3Cc4c(CN3C)cc5OCOc5c4OC PLPRGLOFPNJOTN-UHFFFAOYSA-N 0.000 description 2
- 229960004708 noscapine Drugs 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- IRGJVQIJENCTQF-UHFFFAOYSA-N tritoqualine Chemical compound CN1CCC2=CC=3OCOC=3C(OC)=C2C1C1C2=C(OCC)C(OCC)=C(OCC)C(N)=C2C(=O)O1 IRGJVQIJENCTQF-UHFFFAOYSA-N 0.000 description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- XKXCVGSZHABWJV-UHFFFAOYSA-N 1-(4-methoxy-1,3-benzodioxol-5-yl)-n-methylmethanamine Chemical compound CNCC1=CC=C2OCOC2=C1OC XKXCVGSZHABWJV-UHFFFAOYSA-N 0.000 description 1
- HUMIEJNVCICTPJ-UHFFFAOYSA-N 2,2-dimethoxy-n-methylethanamine Chemical compound CNCC(OC)OC HUMIEJNVCICTPJ-UHFFFAOYSA-N 0.000 description 1
- LILXDMFJXYAKMK-UHFFFAOYSA-N 2-bromo-1,1-diethoxyethane Chemical compound CCOC(CBr)OCC LILXDMFJXYAKMK-UHFFFAOYSA-N 0.000 description 1
- WSFKUKQTVZAWSS-UHFFFAOYSA-N 4-methoxy-[1,3]dioxolo[4,5-g]isoquinoline;hydrochloride Chemical compound [Cl-].C1=[NH+]C=C2C(OC)=C(OCO3)C3=CC2=C1 WSFKUKQTVZAWSS-UHFFFAOYSA-N 0.000 description 1
- UZAYCTATZYAFEY-UHFFFAOYSA-N 5-[(2,2-dimethoxyethylamino)methyl]-1,3-benzodioxol-4-ol Chemical compound COC(OC)CNCC1=CC=C2OCOC2=C1O UZAYCTATZYAFEY-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- 150000003797 alkaloid derivatives Chemical class 0.000 description 1
- 230000003266 anti-allergic effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- BIWVAXGVTGBLEO-UHFFFAOYSA-N n-[(4-hydroxy-1,3-benzodioxol-5-yl)methyl]-n,4-dimethylbenzenesulfonamide Chemical compound C=1C=C2OCOC2=C(O)C=1CN(C)S(=O)(=O)C1=CC=C(C)C=C1 BIWVAXGVTGBLEO-UHFFFAOYSA-N 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 239000004533 oil dispersion Substances 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Landscapes
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60186963A JPS6248678A (ja) | 1985-08-26 | 1985-08-26 | ベンジルアミン誘導体 |
| HU863589A HUT44774A (en) | 1985-08-26 | 1986-08-15 | Process for producing benzylamine derivatives |
| US06/896,961 US4769480A (en) | 1985-08-26 | 1986-08-15 | Benzylamine derivative |
| EP19900401305 EP0387156A3 (en) | 1985-08-26 | 1986-08-22 | A process for preparing cotarnine |
| EP86401866A EP0214051A3 (en) | 1985-08-26 | 1986-08-22 | Benzylamine derivative |
| EP19900402393 EP0404694A3 (en) | 1985-08-26 | 1986-08-22 | 4-hydroxy-8-methoxy-2-methyl-6, 7-methylenedioxy-1,2,3,4-tetrahydroisoquinoline, and process for preparing the same |
| CA000516840A CA1309720C (en) | 1985-08-26 | 1986-08-26 | Benzylamine derivative |
| KR1019860007130A KR900000967B1 (ko) | 1985-08-26 | 1986-08-26 | 벤질아민 유도체 및 그 제법 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60186963A JPS6248678A (ja) | 1985-08-26 | 1985-08-26 | ベンジルアミン誘導体 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6248678A JPS6248678A (ja) | 1987-03-03 |
| JPH0511114B2 true JPH0511114B2 (ko) | 1993-02-12 |
Family
ID=16197788
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60186963A Granted JPS6248678A (ja) | 1985-08-26 | 1985-08-26 | ベンジルアミン誘導体 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6248678A (ko) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4880963B2 (ja) * | 2005-09-27 | 2012-02-22 | パナソニック電工株式会社 | プローブ支持具、プローブ装置、生体内成分測定装置 |
-
1985
- 1985-08-26 JP JP60186963A patent/JPS6248678A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6248678A (ja) | 1987-03-03 |
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